Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones

ABSTRACT

Compounds of the formula ##STR1## wherein R is halogen, C 1  -C 4  alkoxy, C 1  -C 4  alkyl, C 1  -C 4  haloalkyl, cyano, nitro, S(O) n  R wherein R is C 1  -C 4  alkyl and n is the integer 0, 1 or 2; and R 2  through R 8  are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

Application is a division of application Ser. No. 880,370, filed June 30, 1986, now U.S. Pat. No. 4,780,127, which is a continuation-in-part application of application Ser. No. 302,134, filed Nov. 29, 1985, now abandoned; which in turn is a continuation-in-part of application Ser. No. 683,884, filed Dec. 20, 1984, now abandoned.

Applicants specifically incorporate by reference the contents of the above listed U.S. patent applications.

BACKGROUND OF THE INVENTION

Compounds having the structural formula ##STR2## wherein X can be alkyl, n can be 0, 1, or 2, and R₁ can be phenyl or substituted phenyl are described in Japanese patent application No. 84632-1974 as being intermediates for the preparation of herbicidal compounds of the formula ##STR3## wherein R₁, X, and n are as defined above and R₂ is alkyl, alkenyl, or alkynyl. Specifically taught herbicidal compounds of this latter group are those where n is 2, X is 5,5-dimethyl, R₂ is allyl and R₁ is phenyl, 4-chlorophenyl or 4-methoxyphenyl.

The precursor intermediates for these three specifically taught compounds have no or almost no herbicidal activity.

DESCRIPTION OF THE INVENTION

Embodiment A of this invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this embodiment have the following structural formula ##STR4## wherein

R and R¹ are hydrogen, C₁ -C₄ alkyl, preferably methyl or isopropyl, R^(a) OC(O)--, where R^(a) is C₁ -C₄ alkyl; most preferably R and R¹ are hydrogen;

R² is chlorine, bromine, iodine or C₁ -C₄ alkoxy, preferably methoxy; most preferably R₂ is chlorine, bromine or methoxy;

R³, R⁴ and R⁵ independently are hydrogen or an aliphatic group, preferably: (1) hydrogen; (2) halogen, preferably chlorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl, benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently are hydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2; ##STR5## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄ alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) wherein R^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; or less preferably (13) R³ and R⁴ together can form a ring structure with two adjacent carbon atoms of the phenyl ring.

R³ and R⁴ can also be (14) C₃ -C₅ alkenyloxy (thio) optionally substituted, preferably with halogen or (15) C₃ -C₅ alkynyloxy (thio), optionally substituted, preferably with halogen.

Most preferably, R³ is chlorine, hydrogen, dimethylamino or methoxy. Preferably, R⁴ is hydrogen, chlorine, nitro, SO₂ CH₃, SO₂ N(CH₃)₂ or trifluoromethyl. Preferably, R⁵ is hydrogen.

Embodiment A' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inert carrier threfor. Preferably, the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or C₁ -C₄ alkoxy; more preferably chlorine, bromine or methoxy; most preferably chlorine. The 5-position of the 1,3-cyclohexanedione moiety can be substituted with one or two C₁ -C₄ alkyl groups, preferably methyl, although such a substitution is not preferred.

The compounds of Embodiment A of this invention can have the following four structural formulae because of tautomerism: ##STR6## wherein R, R¹, R², R³, R⁴ and R⁵ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR7## wherein R, R¹, R², R³, R⁴ and R⁵ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals, e.g. lithium, sodium, and potassium, alkaline earth metals, e.g. barium, magnesium, calcium and strontium or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

In the above description of the compounds of this invention, alkyl and alkoxy include both straight and branched configurations; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

Embodiment B of this invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this embodiment have the following structural formula ##STR8## wherein

R¹⁰ is C₁ -C₆ alkyl, preferably C₁ -C₄, more preferably methyl;

R¹¹ is hydrogen or C₁ -C₆ alkyl, preferably C₁ -C₄, more preferably methyl or ##STR9## wherein R^(a) is C₁ -C₄ alkyl or R¹⁰ and R¹¹ together are alkylene having 3 to 6 carbon atoms, most preferably R¹¹ is hydrogen or methyl;

R¹² is chlorine, bromine, iodine, fluorine or C₁ -C₄ alkoxy, preferably methoxy; most preferably R¹² is chlorine, bromine or methoxy;

R¹³ and R¹⁴ independently are (1) hydrogen or an aliphatic group, preferably hydrogen; (2) halogen, preferably, fluorine, chlorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ aliphatic alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl, benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently are hydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2; ##STR10## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄ alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) wherein R^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; (13) C₁ -C₄ alkylthio or less preferably (14) R¹³ and R¹⁴ together can form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached or less preferably (15) R¹³ and R¹⁴ are the groups phenoxy or substituted phenoxy wherein the substituent is halogen or halomethyl or both;

R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are independently the same or different and are selected from the group consisting of hydrogen, C₁ -C₆ alkyl, preferably C₁ -C₄ alkyl, more preferably methyl, most preferably hydrogen or methyl, and their salts;

provided, however, that R¹⁵ and R¹⁶ together may form a substituted or unsubstituted alkylene ring of 2-5 carbon atoms, the preferred substituent being 1 or 2 methyl groups.

More preferably, R¹³ is chlorine, hydrogen, methyl, alkylthio or methoxy. Preferably R¹⁴ is hydrogen, chlorine, nitro, trifluoromethyl, or R^(b) SO_(n) wherein R^(b) is C₁ -C₄ alkyl, preferably methyl and n is the integer 0, 1 or 2, preferably 2.

The compounds of Embodiment B of this invention can have the following four structural formulae because of tautomerism: ##STR11## wherein R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR12## wherein R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium, alkaline earth metals, e.g. barium, magnesium, calcium and strontium, or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

The term "aliphatic group" is used form Embodiments A and B herein in a broad sense to cover a large class of organic groups characterized by being derived from (1) an acylic (open-chain structure) of the paraffin, olefin and acetylene hydrocarbon series and their derivatives or (2) alicyclic compounds. The aliphatic group can have from 1 to 10 carbon atoms.

The term "aromatic group" is used for Embodiment A and B herein in a broad sense to distinguish from the aliphatic group and includes a group derived from (1) compounds having 6 to 20 carbon atoms and characterized by the presence of at least one benzene ring, including monocyclic, bicyclic and polycyclic hydrocarbons and their derivatives and (2) heterocyclic compounds having 5 to 19 carbon atoms which are similar in structure and are characterized by having an unsaturated ring structure containing at least one atom other than carbon such as nitrogen, sulfur and oxygen and derivatives of these heterocyclic compounds.

In the above description of the compounds of this invention alkyl and alkoxy include both straight and branched configurations; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

Embodiment C of this invention relates to certain novel 2-(2'-cyanobenzoyl)cyclohexane-1,3-diones as herbicides. The compounds of of this embodiment have the following structural formula ##STR13## wherein R²¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R²¹ is hydrogen or methyl;

R²² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR14## wherein R^(a) is C₁ -C₄ alkyl, most preferably R²² is hydrogen or methyl; or R²¹ and R²² together are alkylene having 3 to 6 carbon atoms;

R²³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²³ is hydrogen or methyl;

R²⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²⁴ is hydrogen or methyl;

R²⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²⁵ is hydrogen or methyl;

R²⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R²⁶ is hydrogen;

R²⁷ and R²⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R²⁷ is not attached to the 6-position.

Preferably, R²⁷ is in the 3-position. Most preferably R²⁷ is hydrogen and R²⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this embodiment can have the following four structural formulae because of tautomerism: ##STR15## wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These portons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR16## wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

Examples of cations of these bases are inorgaic cations such as alkali metals e.g. lithium, sodium, and potassium organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment D of this invention relates to 2-(2-nitrobenzoyl)-1,3-cyclohexanediones and their use as herbicides.

The compounds have a nitro substitution in the 2-position of the phenyl moiety of their compounds. The nitro substitution imparts exceptional herbicidal activity to the compounds of this invention.

Embodiment D' of this invention is an herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment D have the following structural formula ##STR17## wherein R³¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R³¹ is hydrogen or methyl;

R³² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR18## wherein R^(a) is C₁ -C₄ alkyl, most preferably R³² is hydrogen or methyl; or

R³¹ and R³² together are alkylene having 3 to 6 carbon atoms;

R³³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³ is hydrogen or methyl;

R³⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³⁴ is hydrogen or methyl;

R³⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³⁵ is hydrogen or methyl;

R³⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R³⁶ is hydrogen;

R³⁷ and R³⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R³ is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R³⁷ is not attached to the 6-position.

Preferably, R³⁷ is in the 3-position. Most preferably R³⁷ is hydrogen or C₁ -C₄ alkoxy and R³⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chlorine, bromine, iodine or fluorine.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR19## wherein R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR20## wherein R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

Embodiment E of this invention relates to 2-(2-benzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment E' of this invention is an herbicidal composition comprising an herbicidally active 2-(2-C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl or C₁ -C₄ alkylsulfonyl benzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment E have the structural formula ##STR21## wherein n is the integer 0, 1 or 2, preferably 2;

R⁴⁰ is C.sub. -C₄ alkyl, preferably methyl;

R⁴¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁴¹ is hydrogen or methyl;

R⁴² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR22## wherein R^(a) is C₁ -C₄ alkyl, most preferably R⁴² is hydrogen or methyl; or

R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms;

R⁴³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴³ is hydrogen or methyl;

R⁴⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴⁴ is hydrogen or methyl;

R⁴⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴⁵ is hydrogen or methyl;

R⁴⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁴⁶ is hydrogen;

R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁴⁷ is not attached to the 6-position.

Preferably, R⁴⁷ is in the 3-position. Most preferably R⁴⁷ is hydrogen or 3-chlorine and R⁴⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

The term "C₁ -C₄ " alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chloro, bromo, iodo or fluoro.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR23## wherein n, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR24## wherein n, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium, organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment F of this invention relates to 2-(2-alkylbenzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment F' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inert carrier therefor wherein the 2-position of the benzoyl moiety is substituted with C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionally substituted with halogen, more preferably methyl or trifluoromethyl and the 4-position preferably is substituted with an electron withdrawing group, such as halogen, cyano, trifluoromethyl or nitro. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment F have the following structural formula ##STR25## wherein R⁵⁰ is C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionally substituted with halogen, more preferably methyl and trifluoromethyl;

R⁵¹ is hydrogen or C₁ -C₄ ;l alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁵¹ is hydrogen or methyl;

R⁵² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR26## wherein R^(a) is C₁ -C₄ alkyl, most preferably R⁵² is hydrogen or methyl; or

R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms;

R⁵³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵³ is hydrogen or methyl;

R⁵⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵⁴ is hydrogen or methyl;

R⁵⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵⁵ is hydrogen or methyl;

R⁵⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁵⁶ is hydrogen;

R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) _(R) ^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁵⁷ is not attached to the 6-position.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chloro, bromo, iodo or fluoro.

Preferably, R⁵⁷ is in the 3-position. Most preferably R⁵⁷ is hydrogen and R⁵⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR27## wherein R⁵⁰, R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR28## wherein R⁵⁰, R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

Embodiment G of this invention relates to 2-benzoyl-1,3,5-cyclohexanetriones and their use as herbicides.

Embodiment G' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-substituted-1,3,5-cyclohexanetrione and an inert carrier therefor. The 4- and 6-positions of the 1,3,5-cyclohexanetrione moiety are preferably substituted with groups hereinafter defined, most preferably with all methyl groups. The benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment G have the following structural formula ##STR29## wherein R⁶⁰ is hydrogen; halogen; C₁ -C₂ alkyl, preferably methyl; C₁ -C₂ alkoxy, preferably methoxy; nitro; cyano; C₁ -C₂ haloalkyl, preferably trifluoromethyl; R^(a) SO_(n) -- wherein n is 0 or 2, preferably 2 and R^(a) is C₁ -C₂ alkyl, preferably methyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy. Preferably, R⁶⁰ is chlorine, bromine, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, trifluoromethyl, cyano, nitro, methyl, trifluoromethyl or methylsulfonyl; and

R⁶¹ is hydrogen or C₁ -C₄ alkyl, preferably methyl;

R⁶² is hydrogen or C₁ -C₄ alkyl, preferably methyl; or

R⁶¹ and R⁶² together are C₂ -C₅ alkylene;

R⁶³ is C₁ -C₄ alkyl, preferably methyl;

R⁶⁴ is C₁ -C₄ alkyl, preferably methyl; or

R⁶³ and R⁶⁴ together are C₂ -C₅ alkylene;

R⁶⁵ and R⁶⁶ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined; or (13) --N(R^(c))C(O)R^(d) wherein R^(c) and R^(d) are as defined.

Preferably R⁶⁵ is in the 3-position. More preferably R⁶⁵ is hydrogen, chlorine, fluorine, trifluoromethyl, cyano, C₁ -C₄ alkoxy or C₁ -C₄ thioalkyl. Most preferably, R⁶⁵ is hydrogen. Preferably R⁶⁶ is in the 4-position. Most preferably R⁶⁶ is halogen, cyano, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl or C₁ -C₄ haloalkyl, preferably chloromethyl, difluoromethyl or trifluoromethyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "C₁ -C₄ haloalkyl" includes the alkyl groups defined above under C₁ -C₄ alkyl in which one or more hydrogens is replaced by chlorine, bromine, iodine or fluorine.

Salts of the above-described compounds (as defined hereinafter) are included within the scope of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR30## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by reaction with a base to form a salt having an anion of the followig four resonance forms: ##STR31## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals, e.g., lithium, sodium and potassium; the alkaline earth metals, e.g. calcium and magnesium or ammonium or organic cations such as substituted ammonium, sulfonium, sulfoxonium or phosphonium wherein the substituents are aliphatic or aromatic groups.

Those skilled in the art will recognize in considering the salts of this invention that varying degrees os association between the anion and cation will exist depending upon the nature of the cation. In some instances with a suitable cation, such as copper, the salt can exist in a chelated form.

The compounds of this invention and their salts are active herbicides of a general type. That is, they are herbicidally effective against a wide range of plant species. The method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above-described compounds to the area where control is desired.

The compounds of Embodiments A and A' of the present invention can be prepared by the following general method. ##STR32##

Generally, mole amounts of the dione and substituted benzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants and the zinc chloride are combined in a solvent such as methylene chloride. A slight mole excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be prepared according to the teaching of T. S. Oakwood and C. A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compound of Embodiments A and A' of this invention.

EXAMPLE 1-A,A' 2-(2,4-Dichlorobenzoyl)-cyclohexane-1,3-dione ##STR33##

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was dissolved in ether and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether and stirred with 6N hydrochloric acid to destroy the salt. The extract was washed with ether to yield 22.15 grams of the desired product m.p. 138°-140° C. (77.7% yield). The structure was confirmed by instrumental analysis.

The compounds of Embodiment B of the present invention can be prepared by the following general method. ##STR34##

Generally, mole amounts of the dione and substituted benzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants and the zinc chloride are combined in a solvent such as methylene chloride. A slight mole excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be prepared according to the teaching of T. S. Oakwood and C. A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compound of Embodiment B of this invention.

EXAMPLE 1-B 4,4-Dimethyl-2-(2,4-dichlorobenzoyl)-cyclohexane-1,3-dione ##STR35##

4,4-Dimethyl-1,3-cyclohexanedione [14.0 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was chromatographed (2% AcOH/CH₂ Cl₂) in 5 g aliquots then reduced on rotavap under reduced pressure at 50° C. for 30 minutes to remove AcOH. This yielded an oil (40% yield). The structure was confirmed by instrumental analysis.

The compounds of Embodiment C of the present invention can be prepared by the following general method. ##STR36##

Generally, in step (1) mole amounts of the dione and substituted benzoyl chloride are used, along with a slight mole excess of triethylamine. The two reactants are combined in a solvent such as methylene chloride. The triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for several hours.

The reaction product is worked up by conventional techniques. ##STR37##

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the treithylamine, preferably 2 moles of the triethylamine and up to 0.5 mole, preferably 0.1 mole of a cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot for about one hour at room temperature and the desired product is recovered by conventional techniques.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol, I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR38## wherein R²⁷ and R²⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are two representative examples of the methods described therein. ##STR39## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (a) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR40## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (b) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following example teaches the synthesis of a representative compound of Embodiment C of this invention.

EXAMPLE 1-C 2-(2'-Cyanobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione ##STR41##

2-Cyanobenzoyl chloride (3.9 g, 24 mmol) and 4,4-dimethyl-1,3-cyclohexanedione (3.3 g, 24 mmol) were dissolved in 75 ml methylene chloride. Triethylamine (5.0 ml, 36 mmol) was added dropwise and the resulting solution stirred for one and one-half hours at room temperature. The solution was washed with water, 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (4.4 ml, 32 mmol) and acetone cyanohydrin (5 drops) were added and the solution stirred for two hours. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether. The ether was washed with water and brine, dried (MgSO₄) and concentrated under vacuum. The residue was purified by silica gel chromatography, yielding 1.2 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiments D and D' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR42## wherein R³¹ through R³⁸ and moderate base are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O--, C₁ -C₄ alkoxy-C(O)--O-- or ##STR43## wherein R³⁷ and R³⁸ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR44## wherein the moderate base and R³¹ through R³⁸ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol., I. L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR45## wherein R³⁷ and R³⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR46## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR47## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR48## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following examples teach the synthesis of representative compounds of Embodiment D and D' of this invention.

EXAMPLE 1-D,D' 2-(2'-Nitrobenzoyl)-1,3-cyclohexanedione ##STR49##

2-Nitrobenzoyl chloride (5.0 g, 27 mmol) and cyclohexanedione (3.0 g, 27 mmol) were dissolved in methylene chloride. Triethylamine (4.9 ml, 35 mmol) was added dropwise and the resulting solution stirred for one hour. The solution was washed with 2 normal hydrochloric acid (2N HCl), water, 5% potassium carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (1 equivalent) and potassium cyanide (40 mol %) were added and the solution stirred for one hour at room temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% potassium carbonate solution. The aqueous extract was acidified and ether was added. Filtration of the resulting mixture yielded 3.2 g of the desired compound (m.p. 132°-135° C.) which was identified by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

EXAMPLE 2-D,D' 2-(2'-Nitrobenzoyl)-5,5-dimethyl-1,3-cyclohexanedione ##STR50##

Triethylamine (3.4 ml, 25 mmol) was added dropwise to a methylene chloride solution of 2-nitrobenzoyl chloride (3.5 g, 19 mmol) and 5,5-dimethylcyclohexanedione (2.4 g, 19 mmol). After stirring for one hour at room temperature an additional 3 equivalents of triethylamine and 0.4 ml acetone cyanohydrin were added. The solution was stirred for 2.5 hours, then washed with 2N HCl and extracted with 5% potassium carbonate solution. The basic extracts were acidified with 2N HCl and extracted with ether. The ether portion was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was recrytallized from ethyl acetate yielding 2.0 g of the desired compound (m.p. 130°-133° C.) which was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiments E and E' of the present invention can be prepared by the following two or three step general method.

The process proceeds via the production of an enol ester intermediate as shown in reacton (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR51## wherein moderate base, and R⁴⁰ through R⁴⁸ are defined herein, and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O--, C₁ -C₄ alkoxy-C(O)--O-- or ##STR52## wherein R⁴⁰, R⁴⁷ and R⁴⁸ in this portion of the moledule are identical with those in the reactant shown above, and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR53##

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetonecyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction as about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effecitvely). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C. ##STR54## wherein n is 1 or 2.

Generally in step (3), a mole of the reaction product of step (2) is reacted with a slight mole or two mole excess of of an oxidizing agent such as m-chloroperbenzoic acid after being dissolved in a solvent such as methylene chloride. After completion of the reaction, the resulting mixture is stripped under vacuum. The residue is purified by silica gel chromatography to yield the desired product.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR55## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR56## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR57## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR58## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as defined and X is chlorine, bromine or iodine.

In reaction (c) the substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following examples teach the synthesis representative compounds of Embodiments E and E' of this invention.

EXAMPLE 1E,E' 2-(2'-Methylthiobenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR59##

2-Methylthiobenzoyl chloride (7.2 g, 39 mmol) and 4,4,6-trimethylcyclohexanedione (5.0 g, 39 mmol) were dissolved in methylene chloride. Triethylamine (7.0 ml, 50 mmol) was added dropwise and the resulting solution stirred for one hour at room temperature. The solution was washed with 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (2.5 equivalents) and acetone cyanohydrin (0.4 ml) were added and the solution stirred for 45 minutes at room temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with hydrochloric acid and extracted with ether. The ether was washed with brine, dried (MgSO₄) and concentrated under vacuum. The residue was purified by trituration with ether, yielding 5.0 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy (nmr), infrared spectroscopy (ir) and mass spectroscopy (ms).

EXAMPLE 2-E,E' 2-(2'-Methanesulfonylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR60##

The benzoyl cyclohexanedione prepared in Example 1 (2.5 g, 7.9 mmol) was dissolved in 40 ml methylene chloride. m-Chloroperbenzoic acid (3.5 g, 16 mmol) was added and the resulting solution was stirred for 45 minutes. The solution was concentrated under vacuum. Purification of the residue by silica gel chromatography yielded 1.7 g of a viscous oil which was identified as the desired compound by nmr, ir and ms.

EXAMPLE 3-E,E' 2-(4'-Trifluoromethyl-2'-methanesulfinylbenzoyl)-4,4-dimethyl-1,3-cyclohexanedione ##STR61##

2-(40'-Trifluoromethyl-2'-methylthiobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione (5.0 g, 14 mmol) (which was prepared according to the method of Example 1) was dissolved in 50 ml methylene chloride. A solution of m-chloroperbenzoic acid (2.4 g-80%, 14 mmol) in 50 ml methylene chloride was added dropwise and the resulting solution was stirred for three hours at room temperature. After concentration under vacuum, the residue was dissolved in ether and washed with 1% hydrochloric acid. A 5% copper(II) acetate solution was added to the ether fraction, followed by hexane. The liquid phase was decanted and the remaining gummy solid stirred with 6N HCl and ether. The ether layer was dried (MgSO₄) and concentrated to give 4.7 of a thick yellow solid. Purification on a centrifugally accelerated thin layer chromatograph (4 mm silica gel, 50:50:1 hexane:ethyl acetate:acetic acid-eluent) yielded 2.4 g of a viscous oil which was identified as the desired compound by nmr, ir and ms.

The compounds of Embodiments F and F' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR62## wherein R⁵⁰ through R⁵⁸ are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O--, C₁ -C₄ alkoxy-C(O)--O-- or ##STR63## wherein R⁵⁰, R⁵⁷ and R⁵⁸ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete.

The reaction product is worked up by conventional techniques. ##STR64## wherein R⁵⁰ through R⁵⁸ are as defined.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 80° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR65## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are four representative examples of the methods described therein. ##STR66## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR67## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR68## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as defined and X is chlorine, bromine or iodine.

The substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following example teachs the synthesis of a representative compound of Embodiments F and F' of this invention.

EXAMPLE 1-F,F' 2-(4'-Bromo-2'-trifluoromethylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR69##

4-Bromo-2-trifluoromethylbenzoyl chloride (4.3 g, 15 mmol) and 4,4,6-trimethyl-1,3-cyclohexanedione (2.3 g, 15 mmol) were dissolved in 100 ml methylene chloride. The solution was cooled with an ice bath and triethylamine (2.1 ml, 15 mmol) in 10 ml methylene chloride was added dropwise. The ice bath was then removed and the resulting solution stirred for 30 minutes at room temperature. The solution was washed with 2N hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue (5.1 g) was dissolved in 20 ml acetonitrile. Triethylamine (3.5 ml, 25 mmol) and 0.4 ml acetone cyanohydrin were added and the solution stirred for two hours at room temperature while protected by a drying tube (calcium sulfate). After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether. The ether was washed with brine, dried (MgSO₄) and concentrated under vacuum. The resulting oil was purified on a silica gel column (80:20:1 hexane:ethyl acetate:acetic acid-eluent), yielding 1.5 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiment G and G' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR70## wherein R⁶⁰ through R⁶⁶ and moderate base are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O--, C₁ -C₄ alkoxy-C(O)--O-- or ##STR71## wherein R⁶⁰, R⁶⁵ and R⁶⁶ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the trione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably is added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR72## wherein the moderate base and R⁶⁰ through R⁶⁶ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the moderate base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably about 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases, e.g., trialkylamines such as triethylamine and inorganic bases such as alkali metal carbonates and phosphates. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the crown ethers.

A number of different solvents are useful in this process, depending on the nature of the acid halide or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangment may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR73## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR74## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR75## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR76## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following example teaches the synthesis of a representative compound of Embodiment G and G' of this invention.

EXAMPLE 1-G,G' 2-(2'-Nitro-4'-chlorobenzoyl)-4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione ##STR77##

2-Nitro-4-chlorobenzoyl chloride (2.2 g, 10 mmol) and 4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione (1.8 g, 10 mmol) were dissolved in methylene chloride. Triethylamine was added and the resulting solution stirred at room temperature for 30 minutes. The solution was washed with 1 normal hydrochloric acid (1N HCl), and saturated sodium chloride (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (5 ml, 3.5 equivalents) and acetone cyanohydrin (0.5 g, 0.6 equivalent) were added and the mixture stirred at room temperature for 4 hours. After dilution with ether, the solution was washed with 1N HCl and extracted with 5% K₂ CO₃. The basic extract was acidified with HCl and extracted with ether. The ether extract was washed with brine, dried over MgSO₄ and concentrated under vacuum, yielding 2.2 g of crude product. This was recrystallized from benzene to remove syncarpic acid still present. Concentration of the mother liquor under vacuum gave 1.7 g of the desired product as an oil, which solidified on standing (m.p. 76°-82° C.). It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The following are tables of certain selected compounds of Embodiments A-G' that are preparable according to the procedures described herein. Compound numbers are assigned to each compound and are used throughout the remainder of the application.

                                      TABLE I-A                                    __________________________________________________________________________      ##STR78##                                                                     Cmpd.                                         n.sub.D.sup.30 or                No. R         R.sup.1                                                                           R.sup.2                                                                            R.sup.3    R.sup.4  R.sup.5                                                                             m.p. °C.                  __________________________________________________________________________      1A CH.sub.3  CH.sub.3                                                                          Cl  H          H        H    1.5613                            2A CH.sub.3  CH.sub.3                                                                          Cl  H          4-Cl     H    1.5655                            3A CH.sub.3  CH.sub.3                                                                          Cl  H          H        6-Cl 103-108                           4A*                                                                               H         H  Cl  H          4-Cl     H    138-140                           5A CH.sub.3  CH.sub.3                                                                          Br  H          H        H                                      6A CH.sub.3  CH.sub.3                                                                          Cl  H          H        5-Cl 74-77                             7A H         H  Cl  H          H        5-Cl 104-107                           8A H         H  Br  H          H        H    93-96                             9A H         H  Cl  H          H        H    79-87                            10A H         H  I   H          H        H    66-70                            11A H         H  Cl  H          4-NO.sub.2                                                                              H    118-122                          12A H         H  Cl  H          H        6-Cl 143-148                          13A H         H  Cl  H          H        5-Br 109-115                          14A H         H  I   3-I        H        5-I  164-167                          15A H         H  Cl  H          H        5-CH.sub.3                                                                          60-65                            16A H         H  Cl  H          4-CH.sub.3                                                                              H    79-86                            17A H         H  Cl  H          4-CH.sub.3 O                                                                            H    60-63                            18A H         H  Cl  3-Cl       H        6-Cl                                  19A H         H  Cl  H          H        5-CH.sub.3 O                                                                        77-80                            20A H         H  Cl  3-Cl       H        H    80-90                            21A H         H  Cl  H          H        5-CF.sub.3                                                                          74-75                            22A H         H  Cl  H          H        5-NO.sub.2                                                                          140-143                          23A H         H  Cl  3-Cl       4-Cl     H    152-154                          24A H         H  Cl  3-Cl       4-CH.sub.3 O                                                                            H    169-170                          25A H         H  Cl  H          4-Br     H    104-107                          26A CH.sub.3  CH.sub.3                                                                          CH.sub.3 O                                                                         H          H        H    104-108                          27A H         H  Cl  H                                                                                          ##STR79##                                                                              H                                     28A H         H  Br  H          H        (a)                                   29A H         H  CH.sub.3 O                                                                         3-CH.sub.3 O                                                                              H        H    75-79                            30A H         H  CH.sub.3 O                                                                         H          H        5-CH.sub.3 O                                                                        89-92                            31A H         H  Br  H          4-CH.sub.3 O                                                                            5-CH.sub.3 O                                                                        92-96                            32A H         H  Br  H          (4)-OCH.sub.2 O(5)                                                                           63-68                            33A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-Cl     H    86-89                            34A H         H  Cl  3-Cl       H        5-Cl                                  35A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       H        5-Cl 105-109                          36A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-Cl     5-Cl 137-139                          37A H         H  Cl  3-Cl       4-Cl     5-Cl 106-110                          38A H         H  Cl  H          4-Cl     5-Cl 108-111                          39A                                                                                 ##STR80##                                                                               H  Cl  H          4-Cl     H                                     40A                                                                                 ##STR81##                                                                               H  Cl  H          4-Cl     H                                     41A CH(CH.sub.3).sub.2                                                                       H  Cl  H          4-Cl     H                                     42A CH(CH.sub.3).sub.2                                                                       H  Cl  3-Cl       4-Cl     H                                     43A H         H  Cl  H          4-F      H                                     44A sodium salt of Compound No. 23            85-94                            45A isopropylamine salt of Compound No. 23    160-165                          46A triethylamine salt of Compound No. 23     82-85                            47A potassium salt of Compound No. 23         107-106                          48A triethanolammonium salt of Compound No. 39                                 49A sodium salt of Compound No. 43            60-63                            50A CH(CH.sub.3).sub.2                                                                       H  Cl  3-CH.sub.3 O                                                                              4-Br     H                                     51A H         H  Cl  H          4-CH.sub.3 SO.sub.2                                                                     H    140-141                          52A H         CH.sub.3                                                                          Cl  H          4-Cl     H                                     53A i-C.sub.4 H.sub.9                                                                        H  Cl  H          4-Cl     H                                     54A i-C.sub.3 H.sub.7                                                                        H  Cl  3-CH.sub.3 O                                                                              H        H                                     55A CH.sub.3  CH.sub.3                                                                          Cl  H          4-CH.sub.3 SO.sub.2                                                                     H                                     56A CH.sub.3  CH.sub.3                                                                          Cl  3-CH.sub.3 4-Cl     H                                     57A H         H  Cl  3-CH.sub.3 4-Cl     H    56-64                            58A H         H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                              H     98-102                          59A H         H  Cl  3-Cl       4-C.sub.2 H.sub.5 SO.sub.2                                                              H     98-109                          60A H         H  Cl  H          4-C.sub.3 H.sub.7 SO.sub.2                                                              H    semi-solid                       61A H         H  Cl  3-CH.sub.3 O                                                                              4-CH.sub.3 SO.sub.2                                                                     H    48-59                            62A CH.sub.3  CH.sub.3                                                                          Cl  H          4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H    semi-solid                       63A H         H  Cl  3-Cl       4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H      145-148.5                      64A H         H  Cl  3-C.sub.2 H.sub.5 S                                                                       4-C.sub.2 H.sub.5 SO.sub.2                                                              H    oil                              65A CH.sub.3  CH.sub.3                                                                          Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                              H    103-108                          66A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-C.sub.2 H.sub.5 SO.sub.2                                                              H    108-114                          67A i-C.sub.3 H.sub.7                                                                        H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                              H    brown gum                        68A H         H  Cl  3-Cl       4-CH.sub.3 SO.sub.2                                                                     H    145-154                          69A i-C.sub.3 H.sub.7                                                                        H  Cl  3-Cl       4-CH.sub.3 SO.sub.2                                                                     H                                     70A H         H  Br  H          4-CH.sub.3 SO.sub.2                                                                     H    brown gum                        71A H         H  Cl  H          4-i-C.sub.3 H.sub.7 SO.sub.2                                                            H    semi-solid                       72A H         H  Cl  H          4-CH.sub.3 S                                                                            H    74-77                            73A H         H  Cl  3-Cl       4-CH.sub.3 S                                                                            H                                     74A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H    120-123                          75A H         H  Cl  H          4-n-C.sub.4 H.sub.9 SO.sub.2                                                            H    semi-solid                       76A CH.sub.3  CH.sub.3                                                                          Cl  H          4-n-C.sub.4 H.sub.9 SO.sub.2                                                            H                                     77A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-CH.sub.3 SO.sub.2                                                                     H    semi-solid                       78A H         H  Cl  3-CH.sub.3 O                                                                              4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H    golden gum                       79A CH.sub.3  CH.sub.3                                                                          Cl  H          4-i-C.sub.3 H.sub.7 SO.sub.2                                                            H    125-128                          80A CH(CH.sub.3).sub.2                                                                       H  CH.sub.3 O                                                                         3-Cl       5-Cl     H                                     81A H         H  Cl  3-CH.sub.3 O                                                                              4-Br     H    101-111                          82A H         H  Cl  3-CH.sub.3 4-Cl     H    56-64                            83A H         H  Cl  H          4-Cl     5-CH.sub.3 O                                                                        softens >70                      84A CH(CH.sub.3).sub.2                                                                       H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-Br     H                                     85A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-Br     H    101-104                          86A H         H  Cl  H          4-i-C.sub.4 H.sub.9 SO.sub.2                                                            H    136-140                          87A CH.sub.3  CH.sub.3                                                                          Cl  H          4-i-C.sub.4 H.sub.9 SO.sub.2                                                            H                                     88A H         H  Cl  3-Cl       4-i-C.sub.3 H.sub.7 SO.sub.2                                                            H    173-176                          89A H         H  Cl  3-Cl       4-n-C.sub.4 H.sub.9 SO.sub.2                                                            H    135-138                          90A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-C.sub.2 H.sub.5 SO.sub.2                                                              H    gum                              91A H         H  Cl  3-CH.sub. 3 O                                                                             4-C.sub.2 H.sub.5 SO.sub.2                                                              H    gum                              92A H         H  Cl  3-Cl       4-C.sub.2 H.sub.5 S                                                                     H    91-94                            93A H         H  Cl  3-C.sub.2 H.sub.5 S                                                                       4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H    oil                              94A H         H  Cl  3-C.sub.2 H.sub.5 S                                                                       4-C.sub.2 H.sub.5 S                                                                     H    oil                              95A H         H  Cl  H          4-(CH.sub.3).sub.2 NSO.sub.2                                                            H    oil                              96A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H                                     97A H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                              H    oil                              98A CH.sub.3  CH.sub.3                                                                          Cl  H          4-(CH.sub.3).sub.2 NSO.sub.2                                                            H    oil                              99A H         H  Cl  H          4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                     H    90-92                            100A                                                                               CH.sub.3  CH.sub.3                                                                          Cl  H          4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                     H                                     101A                                                                               H         H  Cl  H          4-C.sub.2 H.sub.5 S                                                                     H                                     102A                                                                               H         H  Cl  H          4-n-C.sub.3 H.sub.7 S                                                                   H                                     103A                                                                               H         H  Cl  H          4-i-C.sub.3 H.sub.7 S                                                                   H                                     104A                                                                               H         H  Cl  H          4-C.sub.2 H.sub.5 SO                                                                    H                                     105A                                                                               H         H  CH.sub.3 O                                                                         H          4-NO.sub.2                                                                              H    semi-solid                       106A                                                                               H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-Br     H                                     107A                                                                               H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-CH.sub.3 SO.sub.2                                                                     H     96-100                          108A                                                                               H         H  Cl  3-allyloxy 4-CH.sub.3 SO.sub.2                                                                     H    semi-solid                       109A                                                                               H         H  Cl  3-CH.sub.3 C(O)NH                                                                         4-Cl     H    155-160                          110A                                                                               H         H  Cl  3-Cl       4-n-C.sub.3 H.sub.7 S                                                                   H                                     111A                                                                               H         H  Cl  3-CH.sub.3 O                                                                              4-NO.sub.2                                                                              H    150-153                          112A                                                                               H         H  Cl  3-allyloxy 4-C.sub.2 H.sub.5 SO.sub.2                                                              H                                     113A                                                                               H         H  Cl  3-CH.sub.2 BrCHBrCH.sub.2 O                                                               4-C.sub.2 H.sub.5 SO.sub.2                                                              H                                     114A                                                                               H         H  Cl  3-n-C.sub.4 H.sub.9 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                              H    gum                              115A                                                                               H         H  Cl  3-i-C.sub.4 H.sub.9 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                              H                                     116A                                                                               H         H  Cl  H          4-allylthio                                                                             H                                     117A                                                                               CH.sub.3  CH.sub.3                                                                          Cl  H          4-NO.sub.2                                                                              H                                     118A                                                                               H         H  Cl  3-CH.sub.3 C(O)N(CH.sub.3)                                                                4-Cl     H                                     119A                                                                               H         H  Cl  3-i-C.sub.3 H.sub.7 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                              H                                     120A                                                                               H         H  Cl  3-CH.sub.2 ClCH.sub.2 CH.sub.2 O                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                              H    gum                              121A                                                                               H         H  Cl  H          4-t-C.sub.4 H.sub.9 S                                                                   H                                     122A                                                                               H         H  Cl  3-CH.sub.3 O                                                                              4-C.sub.2 H.sub.5 S                                                                     H                                     123A                                                                               H         H  Cl  H          4-CF.sub.3                                                                              H                                     124A                                                                               H         H  Cl  H          4-Cl     6-Cl                                  125A                                                                               H         H  Cl  3-CH.sub.3 C(O)N(CH.sub.3)                                                                H        H    131-135                          126A                                                                               H         H  Cl  3-CH.sub.3 C(O)NH                                                                         H        H                                     127A                                                                               H         H  Cl  3-(CH.sub.3).sub.2 N                                                                      4-Cl     H                                     128A                                                                               CH.sub.3  H  Cl  3-CH.sub.3 O                                                                              4-CH.sub.3 SO.sub.2                                                                     H    117-122                          129A                                                                               H         H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                              H                                     130A                                                                               H         H  Br  H          H        H                                     131A                                                                               H         H  Br  H          4-C.sub.2 H.sub.5 OC(O)                                                                 H                                     132A                                                                               H         H  Cl  H          4-CN     H    183-184                          133A                                                                               H         H  Cl  3-CH.sub.3 C(O)NH                                                                         H        6-NO.sub.2                            134A                                                                               H         H  Cl  3-(CH.sub.3).sub.2 N                                                                      H        H                                     135A                                                                               H         H  Cl  3-Cl       4-ClCH.sub.2 CH.sub.2 SO.sub.2                                                          H                                     __________________________________________________________________________      * = Prepared in Example 1A.                                                    ##STR82##                                                                

                                      TABLE I-B                                    __________________________________________________________________________      ##STR83##                                                                     Compound                                                                       Number                                                                               R.sup.10 R.sup.11                                                                           R.sup.12                                                                           R.sup.13                                                                             R.sup.14  R.sup.15                                                                          R.sup.16                                                                          R.sup.17                                                                          R.sup.18                       __________________________________________________________________________      1B                                                                                   ##STR84##                                                                              H   Cl  H     4-Cl      H  H  H  H                               2B                                                                                   ##STR85##                                                                              CH.sub.3                                                                           Cl  H     4-Cl      H  H  H  H                               3B   triethanolammonium salt of Compound No. 2                                 4B   triethanolammonium salt of Compound No. 7                                 5B                                                                                   ##STR86##                                                                              CH.sub.3                                                                           Cl  3-Cl  4-Cl      H  H  H  H                               6B   triethanolammonium salt of Compound No. 5                                .sup. CH.sub.3a                                                                               CH.sub.3                                                                           Cl  H     4-Cl      H  H  H  H                               8B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-Cl      CH.sub.3                                                                          H  H  H                               9B   CH.sub.3 n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl      H  H  H  H                              10B   CH.sub.3 H   Cl  H     4-Cl      H  H  H  H                              11B   CH.sub.3 H   Cl  H     4-Cl      CH.sub.3                                                                          H  H  H                              12B   C.sub.5 H.sub.10                                                                            Cl  H     4-Cl      H  H  H  H                              13B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-Cl      H  H  H  H                              14B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-Cl      CH.sub.3                                                                          H  H  H                              15B   i-C.sub.3 H.sub.7                                                                       H   Cl  3-Cl  4-Cl      H  H  H  H                              16B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              17B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 SO.sub.2                                                                      CH.sub.3                                                                          H  H  H                              18B   CH.sub.3 H   Cl  H     4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              19B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              20B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              21B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              22B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                               CH.sub.3                                                                          H  H  H                              23B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              24B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              25B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-Cl      H  H  H  H                              26B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-Cl      H  H  H  H                              27B   CH.sub.3 C.sub.2 H.sub.5                                                                    Cl  H     4-Cl      H  H  H  H                              28B   CH.sub.3 CH.sub.3                                                                           Cl  H     H         H  H  H  H                              29B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-Br      H  H  H  H                              30B   CH.sub.3 CH.sub.3                                                                           Cll H     4-Br      H  H  H  H                              31B   CH.sub.3 C.sub.2 H.sub.5                                                                    Cl  3-Cl  4-Cl      H  H  H  H                              32B   n-C.sub.3 H.sub.7                                                                       H   Cl  H     4-Cl      H  H  H  H                              33B                                                                                   ##STR87##                                                                              n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl      H  H  H  H                              34B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              35B   CH.sub.3 CH.sub.3                                                                           Cl  3-i-C.sub.3 H.sub.7 O                                                                4-Br      H  H  H  H                              36B   CH.sub.3 CH.sub.3                                                                           Cl  H     6-F       H  H  H  H                              37B   i-C.sub.3 H.sub.7                                                                       H   Cl  3-Cl  4-Cl      H  H  H  H                              38B   CH.sub.3 CH.sub.3                                                                           Cl  3-OC.sub.2 H.sub.5                                                                   4-Br      CH.sub.3                                                                          H  H  H                              39B   i-C.sub.3 H.sub.7 OC(O)                                                                 H   Cl  H     4-Cl      H  H  H  H                              40B   C.sub.2 H.sub.5 OC(O)                                                                   n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl      H  H  H  H                              41B   C.sub.5 H.sub.10                                                                            Cl  H     4-Cl      H  H   H H                              42B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-Cl      H  H  CH.sub.3                                                                          H                              43B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              44B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              45B   CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         3-CH.sub.3 O                                                                         H         H  H  H  H                              46B   CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     4-Cl      H  H  H  H                              47B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-Br      CH.sub.3                                                                          H  H  H                              48B   CH.sub.3 CH.sub.3                                                                           Br  H     H         H  H  H  H                              49B   CH.sub.3 CH.sub.3                                                                           I   H     H         H  H  H  H                              50B   CH.sub.3 CH.sub.3                                                                           F   H     H         H  H  H  H                              51B   CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     H         H  H  H  H                              52B   CH.sub.3 CH.sub.3                                                                           Cl  3-allyloxy                                                                           4-Br      H  H  H  H                              53B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 SO.sub.2                                                                      H  H  CH.sub.3                                                                          H                              54B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         4-Br      CH.sub.3                                                                          H  H  H                              55B   CH.sub.3 CH.sub. 3                                                                          Br  H     4-CN      H  H  H  H                              56B   CH.sub.3 CH.sub.3                                                                           Cl  H     4N(CH.sub.3)SO.sub.2 CF.sub.3                                                            H  H  H  H                              57B   CH.sub.3 CH.sub.3                                                                           Cl  3-NO.sub.2                                                                           H         H  H  H  H                              58B   CH.sub.3 CH.sub.3                                                                           C.sub.2 H.sub.5 O                                                                  H     4-Cl      H  H  H  H                              59B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              60B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              61B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              62B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              63B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.4 H.sub.9 SO.sub.2                                                             CH.sub.3                                                                          H  H  H                              64B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                               CH.sub.3                                                                          H  H  H                              65B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-F       H  H  H  H                              66B   CH.sub.3 H   Cl  3-CH.sub.3 O                                                                         4-Br      H  H  H  H                              67B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         H         H  H  H  H                              68B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              69B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              70B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              71B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              72B   CH.sub.3 CH.sub.3                                                                           Cl  Cl    4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              73B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              74B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              75B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-Br      H  H  H  H                              76B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              77B   CH.sub.3 CH.sub.3                                                                           Cl  3-n-C.sub.3 H.sub.7 O                                                                4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              78B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-(CH.sub.3).sub.2 NSO.sub.2                                                             H  H  H  H                              79B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 S                                                                         4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              80B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              81B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              82B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                      H  H  H  H                              83B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              84B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 S                                                                    CH.sub.3                                                                          H  H  H                              85B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 S(O)                                                                   H  H  H  H                              86B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.3 H.sub.7 S                                                                    H  H  H  H                              87B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.3 H.sub.7 S                                                                    H  H  H  H                              88B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-t-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              89B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.3 H.sub.7 S                                                                    CH.sub.3                                                                          H  H  H                              90B   CH.sub. 3                                                                               CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                             CH.sub.3                                                                          H  H  H                              91B   CH.sub.3 CH.sub.3                                                                           Cl  *     4-Cl      H  H  H  H                              92B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.2CHCH.sub.2 S                                                                   H  H  H  H                              93B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              94B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-CH.sub.3 S                                                                             CH.sub.3                                                                          H  H  H                              95B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 S                                                                             H  H  H  H                              96B   CH.sub.3 CH.sub.3                                                                           Cl  3-i-C.sub.3 H.sub.7 O                                                                4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              97B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              98B   CH.sub.3 CH.sub.3                                                                           Cl  **    4-Cl      H  H  H  H                              99B   CH.sub.3 CH.sub.3                                                                           Cl  **    H         H  H  H  H                              100B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-CH.sub.3 S                                                                             H  H  H  H                              101B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     4-NO.sub.2                                                                               H  H  H  H                              102B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     4-CF.sub.3                                                                               H  H  H  H                              103B  CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO                                                                   H  H  H  H                              104B  CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO                                                                   CH.sub.3                                                                          H  H  H                              __________________________________________________________________________      .sup.a Prepared in Example IB.                                                 * = 3CH.sub.3 C(O)NH                                                           ** = 3CH.sub.3 C(O)N(CH.sub.3)                                           

The following additional compounds can be prepared by the general method hereinbefore taught.

                                      TABLE I-B                                    __________________________________________________________________________      ##STR88##                                                                     R.sup.10                                                                            R.sup.11                                                                            R.sup.12                                                                           R.sup.13                                                                              R.sup.14                                                                              R.sup.15                                                                           R.sup.16                                                                           R.sup.17                                                                           R.sup.18                               __________________________________________________________________________     CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      i-C.sub. 3 H.sub.7                                                                  H    Cl  H      4-Cl   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-Cl   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-Cl   H   H   H    H                                     C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub. 5 H.sub.10                                                                        Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub. 2                                                           H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                       H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.3                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H    H                                     CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-n-C.sub.3 H.sub.7 O                                                                 4-Br   H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  H      4-NO.sub.2                                                                            H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-C.sub.2 H.sub.5 O                                                                   4-CH.sub.3 S                                                                          H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  H      4-CN   H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-(CH.sub.3).sub.2 N                                                                  4-Cl   H   H   H   H                                      __________________________________________________________________________

                  TABLE I-C                                                        ______________________________________                                          ##STR89##                                                                     Comp.                                          n.sub.D.sup.30 or               No.   R.sup.21                                                                              R.sup.22                                                                              R.sup.23                                                                            R.sup.24                                                                            R.sup.25                                                                            R.sup.26                                                                            R.sup.27  R.sup.28                                                                    m.p.                            ______________________________________                                         .sup. 1C.sup.a                                                                       CH.sub.3                                                                              CH.sub.3                                                                              H    H    H    H    HH     oil                             2C    H      H      H    H    H    H    HCN    124-                                                                           140° C.                  ______________________________________                                          .sup.a Prepared in Example IC.                                           

                                      TABLE I-D                                    __________________________________________________________________________      ##STR90##                                                                     Comp.                                                                          No. R.sup.31                                                                          R.sup.32                                                                           R.sup.33                                                                           R.sup.34                                                                          R.sup.35                                                                          R.sup.36                                                                          R.sup.37                                                                            R.sup.38 n.sub.D.sup.30 or                        __________________________________________________________________________                                           m.p.                                      1D CH.sub.3                                                                          H   H   H  H  H  H    H        viscous oil                               2D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    H        viscous oil                              .sup.  3D.sup.a                                                                    H  H   H   H  H  H  H    H        132-135                                   4D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    H        viscous oil                              .sup.  5D.sup.b                                                                    H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    H        130-133                                    6D                                                                               CH.sub.3                                                                          H   H   H  CH.sub.3                                                                          H  H    H        viscous oil                               7D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    CF.sub.3 52-61                                     8D H  H   H   H  H  H  H    CF.sub.3 88-94                                     9D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    CF.sub.3 89-97                                    10D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3                                                                          H        119-122                                  11D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-Cl H        72-79                                    12D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Cl       118-121                                  13D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-Cl H        118-120                                  14D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-F  H        130-133                                  15D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3 O                                                                        H        139-142                                  16D CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                           H  H  H  H    CF.sub.3 viscous oil                              17D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    NO.sub.2 viscous oil                              18D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Br       viscous oil                              19D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  CH.sub.3                                                                          5-CH.sub.3                                                                          H        viscous oil                              20D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-CH.sub.3                                                                          H        viscous oil                              21D H  H   H   H  H  H  H    F        123-128                                  22D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    F        viscous oil                              23D H  H   H   H  H  H  H    Cl       viscous oil                              24D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CH.sub.3                                                                       130-133                                  25D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2n-C.sub.3 H.sub.7                                                               viscous oil                              26D H  H   H   H  H  H  H    SO.sub.2 CH.sub.3                                                                       157-159                                  27D H  H   H   H  H  H  H    SO.sub.2n-C.sub.3 H.sub.7                                                               120-123                                  28D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-F  H        165-195                                  29D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2C.sub.2 H.sub.5                                                                 oil                                      30D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    SO.sub.2CH.sub.3                                                                        gum                                      31D CH.sub.3                                                                          n-C.sub.4 H.sub.9                                                                  H   H  H  H  H    H        viscous oil                              32D H  H   i-C.sub.4 H.sub.9                                                                  H  H  H  H    H        viscous oil                              33D H  H   H   H  H  H  H    SO.sub.2C.sub.2 H.sub.5                                                                 viscous oil                              34D H  H   H   H  H  H  H    NO.sub.2 viscous oil                              35D H  H   H   H  H  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                              158-159                                  36D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                              120-130                                  37D H  H   H   H  H  H  H    SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       158-163                                  38D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       oil                                      39D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H                                                                                    ##STR91##                                                                              oil                                      40D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    SO.sub.2N(C.sub.2 H.sub.5).sub.2                                                        oil                                      41D H  H   H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      42D H  H   H   H  H  H  H    S(O)n-C.sub.3 H.sub.7                                                                   oil                                      43D H  H   H   H  H  H  H    Sn-C.sub.3 H.sub.7                                                                      oil                                      44D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    Sn-C.sub.3 H.sub.7                                                                      oil                                      45D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Sn-C.sub.3 H.sub.7                                                                      oil                                      46D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    SC.sub.2 H.sub.5                                                                        oil                                      47D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      47D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      48D H  H   H   H  H  H  H    SCH.sub.3                                                                               94-97                                    49D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CF.sub.3 oil                                      50D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SCH.sub.3                                                                               oil                                      51D .sup.c                                                                            H   i-C.sub.3 H.sub.7                                                                  H  H  H  H    H        145-148                                  52D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-CH.sub.3 O                                                                        Br       oil                                      53D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    Cl       oil                                      54D H  H   H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                      55D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                      56D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CH.sub.3 S                                                                              oil                                      57D H  H   H   H  H  H  H                                                                                    ##STR92##                                                                              120-125                                  58D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    NO.sub.2 175-177                                  59D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    NO.sub. 2                                                                               151-153                                  60D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    NO.sub.2 oil                                      61D .sup.c                                                                            H   H   H  H  H  H    H        oil                                      62D .sup.d                                                                            H   H   H  H  H  H    H        oil                                      63D H  H   CH.sub.3                                                                           H  H  H  H    Cl       110-115                                  64D H  H   CH.sub.3                                                                           H  H  H  H    SO.sub.2n-C.sub.3 H.sub.7                                                               oil                                      65D .sup.d                                                                            CH.sub.3                                                                           H   H  H  H  H    Cl       oil                                      66D H  H   H   H  H  H  H    SO.sub.2 CHCl.sub.2                                                                     oil                                      67D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CHCl.sub.2                                                                     oil                                      68D H  H   H   H  H  H  .sup.c                                                                              Br       oil                                      69D H  H   H   H  H  H  H    SO.sub.2 CH.sub.2 Cl                                                                    oil                                      70D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CH.sub.2 Cl                                                                    wax                                      71D .sup.d                                                                            CH.sub.3                                                                           H   H  H  H  H    H        oil                                      72D H  H   H   H  H  H  C.sub.2 H.sub.5 O                                                                   Cl       oil                                      73D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  CH.sub.3 O                                                                          CF.sub.3 oil                                      __________________________________________________________________________      .sup.a Prepared in Example 1D,D'.                                               .sup.b Prepared in Example 2D,D'.                                             .sup.c = C.sub.2 H.sub.5 OC(O)-                                                .sup.d = iC.sub.3 H.sub.7 OC(O)-                                         

                                      TABLE I-E                                    __________________________________________________________________________      ##STR93##                                                                     Comp.                                                                          No. n R.sup.40                                                                          R.sup.41                                                                          R.sup.42                                                                          R.sup.43                                                                          R.sup.44                                                                          R.sup.45                                                                          R.sup.46                                                                          R.sup.47                                                                           R.sup.48                                                                              m.p.                                     __________________________________________________________________________      1E 0 CH.sub.3                                                                          H  H  H  H  H  H  H   H       79-81° C.                         2E 0 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                       3E.sup.a                                                                          0 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          H  H   H      oil                                       4E.sup.b                                                                          2 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          H  H   H      oil                                        5E                                                                               0 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                       6E 2 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                       7E 0 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               Cl      59-64° C.                         8E 2 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               Cl     116-119° C.                        9E 0 CH.sub.3                                                                          H  H  H  H  H  H  H   CF.sub.3                                                                              102-106° C.                       10E 2 CH.sub.3                                                                          H  H  H  H  H  H  H   CF.sub.3                                                                              oil                                      11E 0 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                               49-53° C.                        12E 2 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              oil                                      13E.sup.c                                                                          1 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              oil                                      14E 0 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               SCH.sub.3                                                                             105-107° C.                       15E 1 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               S(O)CH.sub.3                                                                          oil                                      16E 0 CH.sub.3                                                                          H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                      17E 0 CH.sub.3                                                                          H  H  H  H  H  H  H   SCH.sub.3                                                                             101-103° C.                       18E 2 CH.sub.3                                                                          H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                      19E 2 CH.sub.3                                                                          H  H  H  H  H  H  H   SO.sub.2 CH.sub.3                                                                     194-196° C.                       20E 0 CH.sub.3                                                                          H  H  H  H  H  H  3-CH.sub.3                                                                         H       40-42° C.                        21E 2 CH.sub.3                                                                          H  H  H  H  H  H  3-CH.sub.3                                                                         H       80-86° C.                        __________________________________________________________________________      .sup.a Prepared in Example 1E,E'.                                              .sup.b Prepared in Example 2E,E'.                                              .sup.c Prepared in Example 3E,E'.                                        

                                      TABLE I-F                                    __________________________________________________________________________      ##STR94##                                                                     Comp.                                                                          No. R.sup.50                                                                          R.sup.51                                                                          R.sup.52                                                                          R.sup.53                                                                           R.sup.54                                                                          R.sup.55                                                                          R.sup.56                                                                          R.sup.57                                                                           R.sup.58                                                                              n.sub.D.sup.30 or m.p.                    __________________________________________________________________________      1F CH.sub.3                                                                          H  H  H   H  H  H  H   H      35-42° C.                           2F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   H      47-53° C.                           3F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Br     oil                                        4F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CN     oil                                        5F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-NO.sub.2                                                                         H      oil                                        6F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  5-Cl                                                                               H      oil                                        7F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                        8F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CH.sub.3 SO.sub.2                                                                     oil                                        9F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-Cl                                                                               H      oil                                       10F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       11F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       12F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   n-C.sub.3 H.sub.7 SO.sub.2                                                            oil                                       13F CH.sub.3                                                                          H  H  H   H  H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                       14F CH.sub.3                                                                          H  H  H   H  H  H  H   n-C.sub.3 H.sub.7 SO.sub.2                                                            oil                                       15F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CH.sub.3 S                                                                            oil                                       16F C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Br     oil                                       17F CH.sub.3                                                                          H  H  H   H  H  H  H   CN     oil                                       18F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   F      oil                                       19F CH.sub.3                                                                          H  H  H   H  H  H  H   C.sub.2 H.sub.5SO.sub.2                                                               oil                                       20F CH.sub.3                                                                          H  H  H   H  H  H  3-Cl                                                                               H      65-67° C.                          21F CH.sub.3                                                                          H  H  H   H  H  H  3-I H      oil                                       22F CH.sub.3                                                                          H  H  H   H  H  H  3-NO.sub.2                                                                         H      oil                                       23F CH.sub.3                                                                          H  H  H   H  H  H  3-CN                                                                               H       96-101° C.                        24F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   H      oil                                       25F CF.sub.3                                                                          H  H  H   H  H  H  H   H      oil                                       26F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Br     oil                                       27F CF.sub.3                                                                          H  H  H   H  H  H  H   Cl     82-88° C.                          28F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Cl     oil                                       29F CF.sub.3                                                                          H  H  H   H  H  H  H   C.sub.2 H.sub.5 S                                                                     oil                                       30F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       31F CF.sub.3                                                                          H  H  H   H  H  H  H   CN     oil                                       32F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CN     oil                                        33F.sup.a                                                                         CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   Br     oil                                       34F CH.sub.3                                                                          H  H  H   H  H  H  H   CH.sub.3                                         35F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-Cl                                                                               C.sub.2 H.sub.5 SO.sub.2                                                              115-117° C.                        36F CH.sub.3                                                                          H  H  H   H  H  H  3-Cl                                                                               C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       37F CH.sub.3                                                                          .sup.b                                                                            .sup.b                                                                            H   H  H  H  3-CF.sub.3                                                                         H      oil                                       38F CH.sub.3                                                                          .sup.c                                                                            H  i-C.sub.3 H.sub.7                                                                  H  H  H  3-NO.sub.2                                                                         H       88-108° C.                        39F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CH.sub.3 S                                                                            oil                                       40F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CH.sub.3 S                                                                            oil                                       41F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CH.sub.3 SO.sub.2                                                                     oil                                       42F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CF.sub.3                                                                              oil                                       43F CH.sub.3                                                                          H  H  H   H  H  H  H   CF.sub.3                                                                              114-120° C.                        44F CH.sub.3                                                                          H  H  H   H  H  H  3-Cl                                                                               Cl     oil                                       45F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-Cl                                                                               Cl     oil                                       46F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-CF.sub.3                                                                         H      oil                                       47F CF.sub.3                                                                          H  H  H   H  H  H  H   CH.sub.3 S                                                                            oil                                       48F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CF.sub.3                                                                              oil                                       49F CF.sub.3                                                                          H  H  H   H  H  H  H   CF.sub.3                                                                              oil                                       50F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CF.sub.3                                                                              oil                                       51F CH.sub.3                                                                          H  H  CH.sub.3                                                                           H  H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                       52F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       53F CH.sub.3                                                                          H  H  H   H  H  H  H   Br     94-98° C.                          54F CH.sub.3                                                                          H  H  H   H  H  H  .sup.d                                                                             H      oil                                       __________________________________________________________________________      .sup.a Prepared in Example 1F,F'.-                                             .sup.b (CH.sub.2).sub.5                                                         .sup.c C.sub.2 H.sub.5 OC(O)-                                                 .sup.d 3-N(CH.sub.3)COCH.sub.3                                           

                                      TABLE I-G                                    __________________________________________________________________________      ##STR95##                                                                     Comp.                                                                          No. R.sup.60                                                                            R.sup.61                                                                          R.sup.62                                                                          R.sup.63                                                                          R.sup.64                                                                          R.sup.65                                                                            R.sup.66                                                                               m.p. °C.                              __________________________________________________________________________      1G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       112-117                                       2G.sup.(a)                                                                        NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    76-82                                         3G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.3                                                                    .sup. 176-179°                         4G CH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                           5G CF.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             viscous oil                                   6G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.2 Cl                                                                 oil                                           7G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-F     gum                                           8G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-OC.sub.2 H.sub.5                                                                  4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                           9G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.3                                                                    gum                                          10G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCH.sub.3                                                                            gum                                          11G CH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-NO.sub.2                                                                          H       gum                                          12G I    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       gum                                          13G OCH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    gum                                          14G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-OCH.sub.3                                                                         4-Br    gum                                          15G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 nC.sub.3 H.sub.7                                                            gum                                          16G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 N(CH.sub.3).sub.2                                                           gum                                          17G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CN    .sup.  148-150°                       18G SO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       gum                                          19G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             gum                                          20G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    gum                                          21G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCF.sub.3                                                                            gum                                          22G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-OCF.sub.3                                                                            gum                                          23G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-Cl 4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                          24G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-C(O)CH.sub.3                                                                         gum                                          25G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2CH.sub.3                                                                     129-131                                      26G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCH.sub.3                                                                            89-92                                        27G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             115-125                                      28G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CN    87-95                                        __________________________________________________________________________      .sup.(a) prepared in Example 1G,G'.                                      

Herbicidal Screening Tests

As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic compounds which are useful and valuable in controlling various plant species. Selected compounds of this invention were tested as herbicides in the following manner.

Pre-emergence herbicide test. On the day preceding treatment, seeds of eight different weed species are planted in loamy sand soil in individual rows using one species per row across the width of a flat. The seeds used are green foxtail (FT) (Setaria viridis), watergrass (WG) (Echinochloa crusgalli), wild oat (WO) (Avena fatua), annual morningglory (AMG) (Ipomoea lacunosa), velvetleaf (VL) (Abutilon theophrasti), Indian mustard (MD) (Brassica juncea), redroot pigweed (PW) (Amaranthus retroflexus) or curly dock (CD) (Rumex crispus), and yellow nutsedge (YNG) (Cyperus esculentus). Ample seeds are planted to give about 20 to 40 seedlings per row, after emergence, depending upon the size of the plants.

Using an analytical balance, 600 milligrams (mg) of the compound to be tested are weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 60 milliliter (ml) wide-mouth clear bottle and dissolved in 45 ml of acetone or substituted solvent. Eighteen ml of this solution are transferred to a 60 ml wide-mouth clear bottle and diluted with 22 ml of a water and acetone mixture (19:1) containing enough polyoxyethylene sorbitan monolaurate emulsifier to give a final solution of 0.5% (v/v). The solution is then sprayed on a seeded flat on a linear spray table calibrated to deliver 80 gallons per acre (748 L/ha). The application rate is 4 lb/acre (4.48 Kg/ha).

After treatment, the flats are placed in the greenhouse at a temperature of 70° to 80° F. and watered by sprinkling. Two weeks after treatment, the degree of injury or control is determined by comparison with untreated check plants of the same age. The injury rating from 0 to 100% is recorded for each species as percent control with 0% representing no injury and 100% representing complete control.

The results of the tests are shown in the following Tables

                  TABLE II-A                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.  FT     WG     WO   AMG   VL   MD   PW   CD   YNS                          ______________________________________                                         1A   100    90     20   40    65   50   35        80                           2A   80     90     0    30    80   90   20        90                           3A   0      0      0    40    40   40   0         0                            4A   100    100    50   35    100  100  90        95                           5A   100    95     65   35    90   85   50        95                           6A   50     25     0    25    100  100  35        80                           7A   80     90     10   60    100  100  100       80                           8A   95     95     45   40    100  80   95        95                           9A   95     100    55   30    100  90   100       95                           10A  100    100    60   20    85   100  100       95                           11A  85     100    30   40    100  100  100       95                           12A  85     85     90   75    80   95   90        90                           13A  85     75     10   10    85   65   95        90                           14A  40     10     80   0     65   40   65        100                          15A  40     60     20   30    100  30   75        95                           16A  80     80     20   55    75   90   40        95                           17A  20     --     10   25    100  95   85        90                           18A  65     --     30   70    100  100  85        90                           19A  45     60     0    30    40   0    20        60                           20A  30     85     20   40    95   85   40        45                           21A  80     100    0    80    100  100  95        95                           22A  20     10     0    20    75   30   45        10                           23A  45     95     10   0     100  85   100       95                           24A  --     100    0    25    70   90   --        100                          25A  --     100    25   80    100  100  --        100                          26A  40     15     0    0     0    10        0    30                           27A  40     80     10   20    60   50        30   75                           28A  65     75     0    65    100  95        75   55                           29A  100    95     55   10    80   75        85   95                           30A  20     20     20   10    40   40        50   20                           31A  75     95     20   20    100  95        75   10                           32A  90     85     20   0     100  85        75   30                           33A  80     70     0    40    20   40        90   80                           34A  60     40     0    20    95   100       100  60                           35A  0      10     0    0     10   20        20   10                           36A  0      0      0    20    100  100       100  0                            37A  40     0      0    20    100  60        90   --                           38A  10     40     0    20    90   80        20   20                           39A  80     10     0    0     0    0         0    90                           40A  60     0      0    0     0    0         0    90                           41A  100    100    85   40    95   100       100  100                          42A  60     100    25   0     0    0         0    25                           43A  100    100    45   40    80   90        90   100                          44A  90     100    0    60    100  100       100  95                           45A  100    100    0    60    100  100       100  100                          46A  20     60     0    100   100  100       100  20                           47A  60     70     20   100   100  100       100  60                           48A  60     0      0    0     0    0         0    40                           49A  100    100    50   10    60   20        90   100                          50A  100    100    80   10    60   60        90   100                          51A  100    100    90   100   100  100       85   100                          52A  100    100    60   10    100  100       60   100                          53A  0      20     0    0     20   20        0    10                           54A  10     45     10   0     0    0         0    40                           55A  90     100    60   100   100  100       90   100                          56A  40     70     40   40    40   60        70   50                           57A  100    100    90   100   100  100       85   100                          58A  90     95     0    20    20   40        40   100                          59A  95     100    85   75    100  100       90   98                           60A  95     100    50   50    100  100       90   98                           61A  100    100    75   100   100  100       95   95                           62A  100    100    95   75    100  100       100  80                           63A  100    100    40   65    100  100       100  95                           64A  100    100    98   100   100  100       100  90                           65A  100    100    80   100   100  100       100  90                           66A  100    100    75   100   100  100       100  98                           73A  100    100    60   80    100  100       75   90                           74A  100    100    70   80    100  100       80   100                          75A  70     100    0    50    100  100       100  80                           76A  40     90     25   10    100  100       100  10                           77A  100    100    90   100   100  100       85   --                           78A  100    100    80   100   100  100       90   --                           79A  50     100    50   50    95   100       100  60                           80A  0      0      0    0     0    0         0    0                            81A  100    100    50   15    100  100       90   100                          84A  100    100    85   0     0    100       20   100                          88A  60     95     35   95    100  100       95   80                           89A  75     100    40   100   100  100       95   60                           90A  100    100    90   100   100  100       100  85                           105A 80     95     25   0     95   50        70   50                           117A 95     100    0    25    100  100       50   95                           118A 100    100    60   100   100  100       100  85                           121A 95     100    50   75    100  95        100  80                           125A 100    100    50   80    100  100       100  85                           126A 70     100    80   80    100  100       100  80                           127A 100    100    100  100   100  100       --   80                           128A 100    100    100  100   100  100       --   80                           129A 100    100    95   90    100  100       --   80                           131A 70     85     0    20    95   98        95   90                           132A 100    100    95   90    100  100       --   80                           133A 100    100    100  100   100  100       --   80                           135A 100    100    100  80    100  100       --   80                           ______________________________________                                    

                  TABLE II-B                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1B    0      85      10   75    100  80   80    75                             2B    90     100     65   100   100  100  100   100                            4B    100    100     80   60    100  80   90    100                            5B    80     100     20   40    100  100  80    100                            6B    40     100     0    40    100  100  80    100                            7B    100    100     100  80    100  100  90    100                            8B    100    100     60   45    60   60   80    100                            9B    60     100     40   20    60   60   60    100                            10B   100    100     40   5     80   60   80    100                            11B   100    100     90   10    20   20   40    100                            12B   0      20      0    0     10   20   10    0                              13B   100    100     90   40    100  100  100   100                            15B   90     90      50   20    --   100  100   80                             16B   100    100     95   100   100  100  90    100                            17B   100    100     100  100   100  100  100   97                             18B   100    100     85   100   100  100  90    95                             19B   100    100     95   100   100  100  100   95                             20B   100    100     85   100   100  100  100   90                             21B   100    100     100  100   100  100  100   95                             22B   100    100     80   100   100  100  100   90                             25B   100    100     75   80    100  100  100   90                             26B   100    100     65   30    100  100  100   90                             27B   20     95      60   5     100  100  90    100                            28B   100    100     80   20    90   40   80    100                            29B   100    100     70   20    100  100  100   100                            30B   100    100     80   60    100  100  80    100                            31B   80     100     40   10    60   60   80    100                            32B   20     40      10   0     --   60   100   60                             33B   0      10      0    0     10   10   0     0                              34B   100    100     90   80    100  100  90    100                            35B   100    100     90   40    90   90   90    90                             36B   100    100     85   0     95   85   95    90                             37B   90     90      50   20    --   100  100   80                             39B   15     100     0    50    100  80   70    40                             40B   0      10      0    0     10   10   0     0                              41B   0      20      0    0     10   20   10    0                              42B   100    100     90   45    100  100  65    100                            43B   100    100     90   100   100  100  100   90                             44B   100    100     85   100   100  100  100   95                             45B   65     100     0    0     100  20   20    90                             46B   100    100     0    20    100  100  98    85                             47B   100    100     90   85    100  100  100   95                             48B   100    100     85   15    100  100  85    95                             49B   100    100     65   0     100  100  50    50                             50B   80     80      55   0     98   55   80    65                             51B   95     95      10   0     65   0    25    60                             52B   100    100     100  100   100  100  100   50                             53B   100    100     75   100   100  100  100   50                             54B   100    100     60   15    100  100  100   80                             55B   100    100     55   15    100  100  90    95                             56B   100    100     60   20    95   100  90    10                             57B   5      10      0    0     40   20   0     0                              58B   10     40      10   10    95   40   100   80                             59B   100    100     75   80    100  100  100   75                             60B   100    100     90   100   100  100  85    --                             61B   100    100     80   100   100  100  100   --                             62B   95     100     50   95    100  100  85    --                             63B   100    100     70   100   90   100  100   --                             64B   100    100     75   100   100  100  85    --                             65B   100    100     55   40    100  100  90    70                             66B   100    100     65   35    100  100  100   95                             67B   100    100     30   15    100  100  95    90                             71B   100    100     80   100   100  100  80    --                             72B   100    100     40   100   100  100  90    75                             73B   90     100     40   100   100  100  95    50                             74B   100    100     85   95    100  100  90    80                             75B   100    100     100  70    100  100  100   95                             77B   100    100     55   40    100  100  90    70                             81B   90     95      60   10    25   75   90    0                              82B   40     90      20   35    100  --   75    20                             91B   100    100     85   100   100  100  80    90                             101B  85     90      0    0     95   50   50    75                             ______________________________________                                    

                  TABLE II-C                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1C    65     80      65   55    90   90   35    0                              ______________________________________                                    

                  TABLE II-D                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1D    100    100     85   30    100  100  90    90                             2D    100    100     100  50    100  100  95    95                             3D    100    100     85   25    100  100  100   95                             4D    100    100     100  20    100  85   95    90                             5D    100    100     45   25    100  100  90    90                             6D    100    100     95   40    100  100  85    90                             9D    100    100     90   90    100  100  80    90                             10D   100    90      20   10    100  70   100   90                             11D   90     100     50   230   100  100  90    90                             12D   100    100     95   80    100  100  90    90                             13D   40     75      0    10    80   100  100   90                             14D   50     0       0    0     100  80   70    90                             15D   65     95      20   15    100  80   90    85                             17D   100    100     60   30    100  100  90    35                             18D   100    100     100  100   100  100  100   95                             19D   100    100     0    50    100  100  100   95                             20D   75     100     0    25    100  90   65    90                             21D   100    100     100  80    100  100  90    95                             22D   100    100     100  80    100  100  95    95                             23D   100    100     98   95    100  100  100   95                             25D   100    100     80   100   100  100  80    --                             26D   100    100     75   100   100  100  80    --                             27D   90     100     50   100   100  100  100   90                             28D   75     50      50   0     100  100  90    65                             30D   100    100     85   100   100  100  95    90                             31D   85     75      0    25    100  25   0     35                             32D   83     85      35   20    95   100  75    50                             36D   100    100     50   100   100  100  100   75                             37D   20     75      0    20    100  95   100   75                             38D   85     95      40   60    100  100  75    85                             39D   85     95      45   75    100  95   70    90                             51D   60     60      35   0     25   0    0     30                             52D   75     75      0    50    90   75   40    0                              65D   100    100     80   100   100  100  --    80                             ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                  TABLE II-E                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1E    0      0       0    0     0    0    0     20                             2E    25     30      30   0     70   0    40    30                             3E    25     20      0    0     0    0    0     0                              4E    100    100     90   60    100  100  100   90                             5E    50     60      40   50    50   60   90    50                             6E    100    95      50   40    40   60   99    70                             16E   80     100     50   60    100  90   90    90                             20E   100    100     30   15    100  100  90    85                             21E   100    100     --   30    100  95   100   80                             ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                  TABLE II-F                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1F    40     20      0    0     0    0    0     100                            2F    60     70      0    0     0    0    90    100                            3F    100    100     50   50    100  100  85    90                             4F    100    100     90   30    100  85   95    95                             5F    100    100     80   10    100  100  100   95                             6F    20     35      25   15    90   85   40    85                             7F    100    100     90   100   100  100  100   95                             8F    100    100     90   100   100  100  100   95                             9F    100    100     0    0     100  80   100   90                             10F   100    100     100  100   100  100  100   95                             11F   100    100     70   100   100  100  97    95                             12F   100    100     60   100   100  100  100   95                             13F   100    100     60   100   100  100  100   95                             14F   80     100     50   80    100  100  90    90                             15F   100    100     80   100   100  100  100   --                             16F   50     75      0    25    100  100  95    60                             17F   100    100     40   100   100  100  100   85                             18F   100    100     0    20    100  100  80    70                             20F   70     75      0    25    100  95   100   60                             21F   50     60      0    0     100  80   80    60                             22F   100    95      35   25    100  100  90    50                             23F   95     100     40   20    100  100  90    50                             24F   100    100     90   0     45   85   80    90                             25F   100    100     25   60    100  100  100   75                             34F   35     40      10   0     60   25   0     70                             37F   50     60      0    0     60   0    50    0                              38F   35     40      0    0     0    0    0     0                              52F   85     100     30   95    100  100  --    80                             53F   100    100     0    85    100  100  --    80                             54F   100    100     90   25    100  100  --    80                             ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                  TABLE II-G                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.    FT     WG      WO    AMG   VL    MD   YNS                               ______________________________________                                          1G    100    100     90    100   100   100  80                                 2G    100    100     90    100   100   100  80                                 3G    100    100     90    100   100   100  80                                 4G    100    100     90    100   100   100  80                                 5G    100    100     90    100   100   100  80                                 6G*   100    100     100   100   100   --   20                                 7G    100    100     80    100   100   100  80                                 8G    85     100     80    100   100   100  80                                 9G    100    100     80    100   100   100  80                                10G    100    100     80    100   100   100  80                                11G    100    100     80    100   100   100  80                                12G    100    100     80    90    100   100  0                                 13G    100    100     70    100   100   100  0                                 14G    100    100     75    100   100   100  90                                15G    100    100     80    100   100   100  90                                16G    100    100     90    100   100   100  80                                17G    100    100     80    100   100   100  80                                18G    100    100     90    85    100   100  80                                19G    100    100     100   100   100   100  80                                20G    70     95      10    100   100   100  0                                 21G    100    100     100   100   100   100  80                                22G    100    100     90    100   100   100  80                                23G    100    100     100   100   100   100  80                                24G    0      80      0     25    80    70   0                                 25G    100    100     80    100   100   100  80                                26G    100    100     100   80    100   100  80                                27G    100    100     100   100   100   100  80                                28G    100    100     90    100   100   100  80                                ______________________________________                                          A blank (--) indicates that the weed was not tested.                            *Tested at 0.56 kg/ha.                                                  

Post-Emergence Herbicide Test: This test is conducted in an identical manner to the testing procedure for the pre-emergence herbicide test, except the seeds of the eight different weed species are planted 10-12 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foliage of the sprouted plants.

The results of the post-emergence herbicide test are reported in Table III.

                  TABLE III-A                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.  FT     WG     WO    AMG  VL   MD   PW   CD   YNS                          ______________________________________                                         1A   60     70     20    40   60   60   35        60                           2A   30     70     0     50   90   85   30        80                           3A   0      30     0     70   100  90   55        70                           4A   95     98     20    98   100  100  30        95                           5A   80     80     75    50   60   80   0         95                           6A   40     40     10    60   100  100  75        65                           7A   60     75     40    60   100  75   100       75                           8A   85     80     75    70   95   80   90        90                           9A   85     80     75    70   95   80   90        90                           10A  95     85     90    60   95   95   80        95                           11A  50     80     35    55   100  100  95        80                           12A  45     75     50    55   75   60   50        80                           13A  30     60     20    60   80   50   60        70                           14A  20     10     20    50   45   40   40        0                            15A  65     95     0     65   95   30   100       80                           16A  65     80     20    85   85   30   30        80                           17A  75     80     30    70   100  100  85        90                           18A  100    95     10    100  100  100  100       90                           19A  60     80     40    70   100  75   80        90                           20A  65     80     10    85   95   95   100       70                           21A  30     55     0     80   100  80   65        80                           22A  0      30     0     20   45   0    30        20                           23A  85     90     40    85   100  95   100       90                           24A  0      80     0     70   90   74   --        100                          25A  100    100    75    90   100  100  --        100                          26A  45     30     0     40   70   65        0    45                           27A  75     80     30    65   50   45        85   85                           28A  75     60     60    75   100  70        80   25                           29A  85     85     85    75   85   65        65   85                           30A  75     50     20    10   0    0         20   40                           31A  60     60     20    40   40   70        100  40                           32A  60     25     20    40   90   65        20   40                           33A  10     0      0     10   10   10        100  40                           34A  10     10     0     5    50   30        80   0                            35A  0      0      0     10   60   30        40   0                            36A  0      0      0     20   20   20        0    0                            37A  0      0      0     30   40   20        80   0                            38A  10     10     10    20   10   20        20   10                           39A  40     40     20    0    0    0         5    80                           40A  90     70     40    20   60   80        20   65                           41A  60     85     85    20   40   60        100  100                          42A  60     50     40    70   20   40        60   60                           43A  100    80     30    60   100  100       80   100                          44A  80     85     0     60   90   90        100  80                           45A  90     90     10    100  100  100       100  90                           46A  80     100    0     60   100  100       100  100                          47A  100    100    0     60   100  100       100  100                          48A  40     40     20    10   10   10        90   40                           49A  40     40     40    80   100  100       60   60                           50A  80     60     60    50   50   60        80   70                           51A  80     80     80    95   100  100       100  90                           52A  60     60     20    20   40   40        90   60                           53A  10     20     20    0    0    0         0    20                           54A  20     40     20    5    0    0         0    40                           55A  40     40     40    60   60   60        80   90                           56A  100    100    75    80   100  100       100  90                           57A  80     80     80    95   100  100       100  90                           58A  60     70     10    70   10   10        20   80                           59A  100    100    90    100  --   100       100  50                           60A  100    100    100   100  --   100       100  70                           61A  90     85     90    85   --   100       100  80                           62A  100    85     100   75   100  100       100  35                           63A  70     80     20    100  100  100       35   40                           64A  75     75     90    70   90   70        40   40                           65A  100    70     100   55   90   95        100  40                           66A  100    75     100   90   95   95        100  20                           73A  100    100    95    100  100  100       55   30                           74A  100    95     75    100  100  100       85   40                           75A  100    100    30    95   80   100       80   40                           76A  80     80     75    75   100  95        95   25                           77A  80     80     80    90   90   80        90   80                           78A  80     85     75    85   80   95        100  50                           79A  50     65     35    90   100  100       90   --                           80A  40     40     10    20   60   0         0    30                           81A  90     70     60    40   60   60        90   70                           84A  100    100    100   20   40   40        80   60                           88A  100    95     90    100  85   100       100  50                           89A  100    100    75    85   75   85        95   50                           90A  100    85     90    90   85   90        100  55                           91A  100    100    100   100  95   100       95   60                           105A 35     50     --    35   100  80        60   30                           117A 40     60     0     25   50   50        80   --                           118A 95     85     85    100  100  90        80   80                           121A 65     85     40    100  100  100       60   50                           125A 90     95     75    70   100  90        100  60                           126A 40     50     20    40   60   50        100  80                           127A 100    95     100   95   100  100            80                           128A 85     95     80    60   100  95             80                           129A 65     90     60    60   100  98             70                           130A 100    95     95    95   100  100            70                           131A 0      20     0     0    30   75        10   0                            132A 95     100    100   80   95   95             50                           133A 80     95     90    60   85   85             60                           135A 70     100    100   75   100  95             70                           ______________________________________                                    

                  TABLE III-B                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1B    85     95      20   95    100  100  95    95                             2B    90     90      80   100   90   90   --    80                             4B    60     60      90   40    60   60   90    70                             5B    40     60      10   20    40   40   90    80                             6B    40     50      10   60    20   20   60    50                             7B    80     80      80   60    60   90   6     60                             8B    100    80      60   30    80   80   80    80                             9B    70     70      60   40    60   60   80    70                             10B   40     40      60   30    60   60   90    60                             11B   80     90      60   45    90   90   100   80                             12B   25     45      10   20    20   20   60    45                             13B   100    100     95   70    60   60   80    60                             15B   100    60      50   80    90   90   40    60                             16B   60     60      80   80    90   90   60    65                             17B   100    70      90   100   --   90   98    70                             18B   100    85      100  85    --   100  100   65                             19B   100    80      85   100   100  90   100   70                             20B   90     65      90   85    70   60   100   40                             21B   40     40      10   0     0    0    0     0                              22B   40     70      80   90    90   100  95    40                             25B   40     70      40   40    40   60   70    50                             26B   65     70      80   40    90   80   70    80                             27B   100    80      60   20    90   90   80    45                             28B   90     60      60   60    60   60   40    70                             29B   90     70      70   40    70   70   60    60                             30B   100    90      70   50    100  100  80    80                             31B   40     50      20   10    20   20   0     40                             32B   25     40      40   90    100  100  40    40                             33B   20     40      10   60    90   90   60    40                             34B   90     80      80   80    100  100  80    50                             35B   60     50      50   20    60   60   80    60                             36B   100    80      80   75    --   100  100   45                             37B   100    60      50   80    90   90   40    60                             39B   90     80      25   30    30   45   50    30                             40B   20     40      10   60    90   90   60    40                             41B   25     45      10   20    20   20   60    45                             42B   90     80      80   80    100  100  100   70                             43B   80     90      95   97    100  100  100   50                             44B   100    95      95   95    40   100  100   30                             45B   30     65      0    30    45   40   65    50                             46B   70     75      0    65    100  100  50    70                             47B   100    100     100  90    100  100  100   85                             48B   100    65      80   50    100  100  60    60                             49B   60     70      70   40    80   70   30    50                             50B   0      60      40   60    100  90   20    30                             51B   100    75      80   40    100  50   20    30                             52B   90     100     100  100   100  100  100   40                             53B   60     70      70   70    90   65   40    60                             54B   100    100     85   100   100  100  100   60                             55B   95     85      90   100   100  100  90    45                             56B   85     100     0    10    15   95   40    50                             57B   85     70      65   0     0    0    0     35                             58B   20     40      10   15    70   40   35    40                             59B   100    95      100  95    100  95   100   40                             60B   65     75      75   80    90   85   80    60                             61B   80     80      70   95    80   85   80    50                             62B   100    80      25   80    75   80   85    35                             63B   100    100     40   95    95   100  95    50                             64B   75     70      50   90    90   100  90    50                             65B   100    80      80   60    85   60   0     --                             66B   98     90      60   35    --   100  60    90                             67B   70     65      20   15    95   40   70    45                             71B   95     50      50   80    80   80   65    50                             72B   100    85      75   75    65   85   70    60                             73B   100    95      95   85    75   85   95    40                             74B   100    85      95   90    80   95   65    50                             75B   100    80      80   30    50   60   100   40                             81B   50     80      35   70    70   90   80    10                             82B   25     60      50   35    50   90   50    25                             91B   80     60      40   60    75   90   60    75                             101B  10     35      --   30    75   70   40    50                             ______________________________________                                          (--) = Specie did not germinate for some reason.                         

                  TABLE III-C                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1C    98     95      70   60    100  55   100   90                             ______________________________________                                    

                  TABLE III-D                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD    YNS                            ______________________________________                                         1D    95     75      85   70    100  90   85    40                             2D    45     70      95   75    100  90   100   65                             3D    100    80      100  90    --   100  100   80                             4D    100    80      100  100   --   100  85    75                             5D    90     70      45   60    95   70   60    80                             6D    95     75      80   70    100  90   90    65                             9D    100    90      90   100   100  100  95    85                             10D   45     75      10   15    100  100  20    75                             11D   100    70      60   75    100  100  100   45                             12D   100    75      100  100   100  100  90    90                             13D   30     55      0    30    60   60   15    60                             14D   20     65      0    40    70   60   40    25                             15D   20     75      30   20    100  70   60    40                             17D   85     80      50   65    95   95   100   60                             18D   100    95      100  100   100  100  100   75                             19D   20     95      30   100   100  35   30    70                             20D   30     80      15   100   100  45   20    70                             21D   100    80      100  55    100  90   100   80                             22D   100    80      100  60    100  95   95    95                             23D   100    90      90   100   100  100  85    70                             25D   70     75      50   85    90   85   60    75                             26D   100    85      85   95    95   95   90    60                             27D   90     90      60   100   100  100  100   --                             28D   15     45      20   50    75   80   15    30                             30D   100    100     80   85    85   85   100   --                             31D   80     90      100  100   100  100  100   60                             32D   75     85      85   75    75   90   95    50                             36D   35     50      35   70    50   50   35    60                             37D   60     75      15   70    70   90   90    40                             38D   95     90      65   70    90   90   100   50                             39D   95     85      30   50    70   80   100   50                             51D   60     75      60   35    30   60   40    60                             52D   60     75      25   100   100  100  100   75                             65D   70     50      70   90    80   85   --    80                             ______________________________________                                          A blank (--) indicates the weed was not tested.                          

                  TABLE III-E                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD   YNG                             ______________________________________                                         1E    20     20      10   20    40   40   20   40                              2E    0      60      60   50    70   30   0    15                              3E    20     20      0    10    0    20   0    20                              4E    85     90      100  45    75   30   80   65                              5E    55     50      60   50    75   85   65   --                              6E    70     70      50   60    80   70   90   --                              16E   95     95      40   100   100  100  100  90                              20E   95     75      35   40    95   75   35   80                              21E   80     70      30   45    80   90   50   70                              ______________________________________                                          A blank (--) indicates the weed was not tested.                          

                  TABLE III-F                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD   YNG                             ______________________________________                                         1F    60     40      20   30    40   40   50    60                             2F    50     40      10   20    20   20   40    60                             3F    100    100     85   100   100  100  100   75                             4F    100    100     95   85    100  95   100   60                             5F    95     95      100  65    90   25   70    45                             6F    40     30      0    20    90   25   20    70                             7F    100    100     100  100   100  100  100   90                             8F    100    95      100  100   100  100  100   70                             9F    65     65      0    20    80   65   90    80                             10F   100    100     100  100   100  100  100   70                             11F   85     90      90   85    90   80   30    60                             12F   100    90      65   80    100  100  100   50                             13F   100    95      100  100   100  100  90    --                             14F   100    100     100  100   100  100  100   50                             15F   25     35      15   30    80   25   20    0                              16F   100    85      70   75    90   90   50    --                             17F   100    100     100  100   100  100  100   --                             18F   90     85      85   85    90   95   70    40                             20F   40     60      10   60    100  100  100   50                             21F   35     60      10   60    100  100  80    60                             22F   95     95      35   100   100  100  90    50                             23F   100    100     40   100   100  100  90    50                             24F   100    75      100  60    --   100  100   60                             25F   95     95      90   95    100  100  95    35                             34F   50     40      0    35    50   70   30    50                             37F   20     60      0    30    30   50   50    50                             38F   25     50      0    25    25   50   20    20                             52F   0      60      50   50    10   50   --    20                             53F   0      50      0    50    50   50   --    30                             54F   90     75      60   50    50   80   --    80                             ______________________________________                                          A blank (--) indicates the weed was not tested.                          

                  TABLE III-G                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd. No.                                                                              FT     WG      WO   AMG   VL    MD   YNG                               ______________________________________                                          1G     100    95      90   90    100   100  80                                 2G     100    100     100  100   100   100  80                                 3G     100    100     95   100   100   100  90                                 4G     100    100     100  100   100   100  90                                 5G     100    100     100  100   100   100  100                                6G*    10     80      50   75    40    --   0                                  7G     70     75      70   90    90    80   80                                 8G     50     80      70   90    90    80   30                                 9G     70     80      70   90    90    80   30                                10G     75     80      70   80    60    50   70                                11G     70     80      70   80    80    80   80                                12G     100    75      90   75    80    80   80                                13G     60     70      70   100   100   100  80                                14G     20     70      40   60    80    80   70                                15G     90     70      70   75    80    90   70                                16G     50     70      80   60    80    90   70                                17G     90     60      70   65    80    80   80                                18G     30     50      80   95    95    80   70                                19G     100    100     95   90    100   100  80                                20G     10     40      5    70    80    90   70                                21G     95     90      95   95    100   100  70                                22G     80     90      90   80    100   100  70                                23G     90     80      80   80    90    80   30                                24G     0      30      0    40    80    20   0                                 25G     0      20      0    10    10    20   0                                 26G     80     70      70   80    80    80   70                                27G     90     90      90   80    80    90   60                                28G     70     65      50   80    80    80   70                                ______________________________________                                          A blank (--) indicates the weed was not tested.                                *= Tested at 0.56 kg/ha.                                                 

Pre-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 2 lb/acre (2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for pre-emergence activity against a larger number of weed species.

The process was generally similar to the pre-emergence herbicide test described above except that only 300 or 150 milligrams of test compound were weighed out and the application rate was 40 gallons per acre.

Redroot pigweed (PW) and curly dock (CD) were eliminated in this test and the following weed species were added:

    ______________________________________                                         Grasses:                                                                              downy brome    Bromus tectorum                                                                              (DB)                                              annual ryegrass                                                                               Lolium multiflorum                                                                           (ARG)                                             rox-orange sorghum                                                                            Sorghum bicolor                                                                              (SHC)                                             hemp sesbania  Sesbania exaltata                                                                            (SESB)                                            nightshade     Solanum sp.   (SP)                                              cocklebur      Xattiium sp.  (CB)                                       ______________________________________                                    

The results of the 2.24 kg/ha test are shown in Table IV and the results of the 1.12 kg/ha test are shown in Table VI.

Post-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 2 lb/acre (2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for post-emergence activity against the larger number of weed species that are used in the pre-emergent multi-herbicide test.

The process was generally similar to the post-emergence herbicide test described above except that only 300 or 150 milligrams of test compound were weighed out and the application rate was 40 gallons per acre.

The results of the 2.24 kg/ha test are shown in Table V and the results for the 1.12 kg/ha test are shown in Table VII.

                                      TABLE IV-A                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     67A 20 90 25  98 80 60 90 45  90  45 20                                                                               85 85 15                                68A 65 98 98  100                                                                               100                                                                               60 95 100 100 100                                                                               80                                                                               100                                                                               95 100                               69A 65 100                                                                               70  100                                                                               100                                                                               65 95 100 95  70 65                                                                               100                                                                               90 --                                70A 98 100                                                                               100 100                                                                               100                                                                               90 98 90  100 90 60                                                                               100                                                                               95 80                                71A 60 20 100 100                                                                               100                                                                               80 95 35  40  100                                                                               20                                                                               90 100                                                                               40                                72A 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 90  100                                                                               60                                                                               100                                                                               100                                                                               20                                83A 15 45 25  90 15 5  90 45  35  20 0 20 75 --                                86A 20 0  15  60 60 20 70 25  45  100                                                                               20                                                                               100                                                                               15 35                                87A 100                                                                               90 85  100                                                                               85 25 30 35  85  100                                                                               85                                                                               100                                                                               95 40                                __________________________________________________________________________

                                      TABLE VI-A                                   __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 2.24 hg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     86A 60 100                                                                               50  90 50 60 90 70  100 100                                                                               20 100                                                                               20 --                               87A 95 100                                                                               30  100                                                                               80 70 80 95  100 100                                                                               100                                                                               100                                                                               70 --                               __________________________________________________________________________

                                      TABLE V-A                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      82A                                                                               35 100                                                                               85  100                                                                               65 60 90 50  90  60 30 97 90 40                                85A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               20  10  100                                                                               65 100                                                                               100                                                                               30                                92A                                                                               15 20 45  100                                                                               90 40 80 95  95  100                                                                               25 100                                                                               90 40                                93A                                                                               30 75 40  100                                                                               100                                                                               60 90 100 100 100                                                                               35 100                                                                               90 40                                94A                                                                               30 70 40  100                                                                               100                                                                               30 65 95  85  100                                                                               0  100                                                                               90 30                                95A                                                                               0  0  0   85 60 15 70 65  60  100                                                                               80 90 10 20                                96A                                                                               95 100                                                                               98  100                                                                               100                                                                               70 100                                                                               100 95  90 80 100                                                                               95 --                                97A                                                                               100                                                                               100                                                                               98  100                                                                               100                                                                               100                                                                               100                                                                               100 95  100                                                                               70 100                                                                               95 100                               98A                                                                               10 0  0   0  20 25 70 0   20  0  0  80 30 --                                99A                                                                               15 0  0   75 25 0  20 30  60  15 20 30 25 0                                100A                                                                               0  0  0   0  0  0  20 10  0   0  0  15 0  --                               101A                                                                               100                                                                               98 95  100                                                                               100                                                                               70 98 100 100 100                                                                               20 100                                                                               95 --                               102A                                                                               25 20 35  100                                                                               100                                                                               45 95 70  100 100                                                                               60 100                                                                               90 --                               103A                                                                               80 60 45  100                                                                               100                                                                               40 90 65  90  100                                                                               0  100                                                                               95 0                                106A                                                                               100                                                                               100                                                                               60  40 95 35 100                                                                               35  90  100                                                                               70 100                                                                               90 --                               107A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               80 100                                                                               95 30                               108A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               30 100                                                                               95 100                              109A.sup.a                                                                         65 20 85  100                                                                               98 60 90 30  50  100                                                                               50 100                                                                               90 100                              110A                                                                               0  60 30  100                                                                               65 25 65 25  30  100                                                                               0  100                                                                               60 0                                111A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               75 98 100 100 100                                                                               90 100                                                                               -- 70                               112A                                                                               100                                                                               100                                                                               90  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               100                                                                               100                                                                               -- --                               113A                                                                               65 95 40  100                                                                               100                                                                               30 90 70  100 100                                                                               0  100                                                                               -- 30                               114A                                                                               70 100                                                                               25  100                                                                               100                                                                               40 100                                                                               100 100 100                                                                               30 100                                                                               95 80                               115A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               45 100                                                                               85 100                              116A                                                                               25 15 20  100                                                                               65 35 65 45  50  100                                                                               0  100                                                                               95 10                               119A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               95 100                                                                               95 90                               120A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 100                              122A                                                                               80 80 45  100                                                                               60 65 70 100 100 100                                                                               100                                                                               100                                                                               90 100                              123A                                                                               0  100                                                                               50  100                                                                               85 0  60 100 90  100                                                                               80 100                                                                               100                                                                               20                               124A                                                                               25 50 65  90 65 0  40 75  80  100                                                                               40 90 80 60                               __________________________________________________________________________      .sup.a application rate was 0.56 kg/ha.                                  

                                      TABLE VII-A                                  __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      82A                                                                               60 40 10  98 35 10 30 70  100 100                                                                               100                                                                               90 45 --                                85A                                                                               60 60 35  100                                                                               45 60 85 50  100 100                                                                               100                                                                               100                                                                               60 --                                92A                                                                               70 55 20  80 80 45 100                                                                               95  90  80 20 95 70 90                                93A                                                                               90 90 70  95 95 75 90 98  95  85 35 100                                                                               60 90                                94A                                                                               100                                                                               85 45  90 100                                                                               90 100                                                                               100 90  90 30 100                                                                               60 85                                95A                                                                               20 60 0   80 70 0  45 60  75  90 0  65 20 --                                96A                                                                               95 100                                                                               90  95 100                                                                               80 95 100 100 100                                                                               70 100                                                                               70 90                                97A                                                                               100                                                                               100                                                                               95  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               70 100                               98A                                                                               20 0  0   45 10 50 30 20  65  100                                                                               0  75 35 80                                99A                                                                               25 75 15  80 65 10 25 85  100 100                                                                               80 100                                                                               10 --                               100A                                                                               10 35 0   70 50 5  20 30  70  40 0  100                                                                               10 100                              101A                                                                               30 60 25  100                                                                               60 60 80 100 100 100                                                                               30 100                                                                               70 --                               103A                                                                               90 100                                                                               25  100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               15 100                                                                               40 --                               104A                                                                               98 98 25  98 100                                                                               15 100                                                                               100 100 100                                                                               60 100                                                                               95 --                               106A                                                                               75 90 30  90 70 25 100                                                                               100 100 100                                                                               80 100                                                                               75 --                               107A                                                                               100                                                                               100                                                                               80  90 85 100                                                                               100                                                                               100 100 100                                                                               60 100                                                                               40 --                               108A                                                                               100                                                                               100                                                                               65  90 60 95 100                                                                               100 100 100                                                                               90 100                                                                               90 --                               109A.sup.a                                                                         90 60 45  90 70 60 98 95  95  100                                                                               98 80 55 --                               110A                                                                               50 50 20  100                                                                               50 10 40 100 98  98 20 100                                                                               35 45                               111A                                                                               85 90 80  90 70 60 95 100 90  100                                                                               65 100                                                                               80 60                               112A                                                                               100                                                                               100                                                                               90  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               45 100                                                                               95 70                               113A                                                                               70 50 20  90 60 50 80 95  95  100                                                                               60 100                                                                               -- 60                               114A                                                                               85 100                                                                               15  100                                                                               100                                                                               60 00 100 100 100                                                                               100                                                                               100                                                                               60 --                               115A                                                                               100                                                                               100                                                                               45  100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 --                               116A                                                                               80 60 25  90 35 40 45 75  90  100                                                                               40 90 75 60                               119A                                                                               60 70 30  95 70 20 90 100 100 100                                                                               90 100                                                                               30 85                               120A                                                                               75 90 60  95 80 45 100                                                                               100 90  100                                                                               65 100                                                                               35 100                              122A                                                                               60 90 15  100                                                                               30 15 15 100 100 100                                                                               75 100                                                                               45 95                               123A                                                                               0  100                                                                               35  100                                                                               50 15 85 100 100 100                                                                               100                                                                               100                                                                               70 85                               124A                                                                               25 100                                                                               35  40 35 0  40 95  100 100                                                                               100                                                                               100                                                                               85 75                               __________________________________________________________________________      A = Application rate was 0.56 kg/ha.                                           A dash mark (--) is used in Tables II-VII to indicate that no percent          control number was available.                                            

                                      TABLE IV-B                                   __________________________________________________________________________     Pre-Emergence Multi-Weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________      14B                                                                               80 100                                                                               100 100                                                                               100                                                                               80 95 70  60  100                                                                               40                                                                               85 100                                                                               10                                 21B                                                                               85 100                                                                               90  100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               70                                                                               100                                                                               95 100                                24B                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               75                                                                               100                                                                               95 --                                 38B                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               20  10  100                                                                               20                                                                               95 100                                                                               20                                 88B                                                                               75 100                                                                               60  100                                                                               100                                                                               70 60 20  40  100                                                                               0 100                                                                               60 20                                 89B                                                                               20 60 30  85 95 55 40 15  20  65 0 100                                                                               35 50                                 90B                                                                               60 100                                                                               60  100                                                                               100                                                                               45 30 100 100 100                                                                               15                                                                               100                                                                               50 85                                103B                                                                               95 100                                                                               75  100                                                                               100                                                                               50 85 100 100 100                                                                               80                                                                               100                                                                               80 40                                104B                                                                               60 100                                                                               60  100                                                                               100                                                                               45 30 100 100 100                                                                               15                                                                               100                                                                               50 85                                __________________________________________________________________________      (--) = Specie did not germinate for some reason.                         

                                      TABLE V-B                                    __________________________________________________________________________     Post-Emergence Multi-Weed Herbicide Test                                       Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________      24B                                                                               35 25 45  60 65 85 90 100 100 -- 90                                                                               100                                                                               65 --                                 88B                                                                               60 30 30  90 100                                                                               80 100                                                                               100 100 100                                                                               30                                                                               100                                                                               20 100                                89B                                                                               50 70 35  90 60 35 20 100 90  100                                                                               35                                                                               100                                                                               15 100                                90B                                                                               30 100                                                                               40  100                                                                               70 10 25 100 100 100                                                                               30                                                                               90 50 95                                103B                                                                               95 100                                                                               70  100                                                                               65 75 65 100 100 100                                                                               65                                                                               100                                                                               50 100                               104B                                                                               30 100                                                                               40  100                                                                               70 10 25 100 100 100                                                                               30                                                                               90 50 95                                __________________________________________________________________________      (--) = Specie did not germinate for some reason.                         

                                      TABLE VI-B                                   __________________________________________________________________________     Pre-Emergence Multi-Weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      1B 25 10 30  85 55 0  -- 55  --  100                                                                               -- 75 75 35                                23B                                                                               55 95 90  100                                                                               95*                                                                               95 95 98  80  -- 10 100                                                                               95 --                                68B                                                                               65 100                                                                               60  100                                                                               100*                                                                              6  90 100 90  100                                                                               20 100                                                                               30 40                                69B                                                                               70 100                                                                               60  100                                                                               100*                                                                              95 95 100 95  100                                                                               0  100                                                                               85 25                                70B                                                                               60 100                                                                               75  100                                                                               100*                                                                              85 100                                                                               100 90  100                                                                               25 100                                                                               90 25                                76B                                                                               100                                                                               100                                                                               85  100                                                                               100*                                                                              85 98 100 95  -- 35 100                                                                               95 --                                78B                                                                               40 70 15  95 75*                                                                               25 80 65  75  -- 0  100                                                                               80 --                                79B                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               98 100                                                                               100 85  100                                                                               85 100                                                                               95 --                                80B                                                                               98 100                                                                               95  100                                                                               100                                                                               60 98 99  90  100                                                                               35 100                                                                               85 --                                83B                                                                               20 100                                                                               60  100                                                                               100*                                                                              40 90 85  65  100                                                                               0  100                                                                               85 --                                84B                                                                               0  90 25  98 100*                                                                              30 90 20  35  100                                                                               5  100                                                                               50 --                                85B                                                                               80 100                                                                               50  100                                                                               100                                                                               60 90 100 90  100                                                                               0  100                                                                               95 --                                86B                                                                               60 90 40  100                                                                               100                                                                               60 70 35  60  100                                                                               100                                                                               100                                                                               -- --                                87B                                                                               0  90 15  100                                                                               85 15 70 40  60  100                                                                               40 90 20 --                                92B                                                                               20 40 10  95 40 10 60 65  30  100                                                                               0  55 60 0                                 93B                                                                               60 95 20  100                                                                               100                                                                               75 100                                                                               100 100 100                                                                               0  100                                                                               40 35                                94B                                                                               0  80 40  100                                                                               95 25 85 80  40  100                                                                               10 85 55 10                                95B                                                                               98 100                                                                               30  100                                                                               100                                                                               40 90 100 100 100                                                                               40 100                                                                               90 30                                96B                                                                               100                                                                               100                                                                               75  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               60 100                                                                               85 100                               97B                                                                               100                                                                               100                                                                               90  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               60 100                                                                               95 100                               98B                                                                               95 100                                                                               100 100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               50 100                                                                               100                                                                               60                                99B**                                                                             -- 100                                                                               75  100                                                                               100*                                                                              20 75 50  75  95 0  -- 85 30                               100B                                                                               100                                                                               98 98  100                                                                               100                                                                               90 95 100 75  100                                                                               70 100                                                                               95 40                               102B                                                                               0  100                                                                               25  100                                                                               90 75 95 60  60  100                                                                               30 100                                                                               90 --                               __________________________________________________________________________      *seedling johnsongrass (Sroghum halepense) was substituted for roxorgange      sorghum.                                                                       **Application rate was 0.56 kg/ha                                              (--) = Specie did not germinate for some reason.                         

                                      TABLE VII-B                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      1B 45 35 40  90 35 10 -- 60  --  75 -- 60 50 55                                23B                                                                               90 100                                                                               80  90 90*                                                                               90 90 80  90  90 40 70 25 --                                68B                                                                               50 60 40  85 80*                                                                               75 100                                                                               95  90  85 55 100                                                                               40 --                                69B                                                                               70 80 35  90 90*                                                                               80 90 80  85  90 20 90 25 --                                70B                                                                               100                                                                               90 80  100                                                                               100*                                                                              95 100                                                                               100 95  80 30 75 45 90                                76B                                                                               100                                                                               100                                                                               98  100                                                                               100*                                                                              100                                                                               100                                                                               100 100 100                                                                               60 100                                                                               40 --                                78B                                                                               100                                                                               90 80  85 100*                                                                              70 90 100 100 100                                                                               0  90 45 --                                79B                                                                               80 35 45  70 60*                                                                               70 70 45  98  100                                                                               35 90 20 --                                80B                                                                               60 70 25  90 60*                                                                               60 85 70  90  100                                                                               15 100                                                                               25 100                               85B                                                                               95 100                                                                               65  100                                                                               80 90 100                                                                               100 100 100                                                                               25 100                                                                               85 --                                86B                                                                               30 60 20  75 50 50 60 50  65  100                                                                               10 100                                                                               20 80                                87B                                                                               0  0  0   100                                                                               45 20 30 60  90  80 0  100                                                                               30 45                                92B                                                                               20 80 10  85 15 0  30 100 40  100                                                                               0  60 60 30                                93B                                                                               70 100                                                                               25  100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               100                                                                               100                                                                               80 --                                94B                                                                               20 70 30  90 80 30 20 100 100 100                                                                               60 30 30 100                               95B                                                                               60 90 15  95 95 25 90 100 100 100                                                                               75 100                                                                               70 100                               96B                                                                               50 80 0   90 70 30 100                                                                               100 100 100                                                                               40 100                                                                               20 100                               97B                                                                               65 100                                                                               35  100                                                                               75 70 80 100 100 100                                                                               50 100                                                                               50 100                               98B                                                                               95 100                                                                               65  95 90 100                                                                               95 100 100 90 40 80 60 95                                99B**                                                                             -- 100                                                                               95  90 90*                                                                               90 100                                                                               25  80  40 100                                                                               -- 35 75                               100B                                                                               65 75 60  80 75 60 85 100 100 100                                                                               45 100                                                                               65 60                               102B                                                                               30 75 20  80 60 0  40 70  100 100                                                                               30 100                                                                               75 --                               __________________________________________________________________________      *Seedling johnsongram (Sorghum halepense) was substituted for roxorange        sorghum.                                                                       **Application rate was 0.56 kg/ha.                                             (--) = Specie did not germinate for some reason.                         

                                      TABLE IV-C                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     2C  0  100                                                                               0   100                                                                               -- 45 70 65  50  100                                                                               15 100                                                                               90 --                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE V-C                                    __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     2D  0  30 0   100                                                                               -- 0  60 85  95  100                                                                               100                                                                               90 40 --                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IV-D                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      7D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 100                               8D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 --                               16D.sup.a                                                                          70 100                                                                               65  100                                                                               100                                                                               60 98 55  100 100                                                                               90 100                                                                               90 --                               24D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               29D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               30 100                                                                               95 80                               33D 75 15 60  90 90 20 95 100 100 100                                                                               60 100                                                                               95 100                              53D 100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 100                              57D 100                                                                               100                                                                               25  100                                                                               100                                                                               30 25 100 100 100                                                                               100                                                                               100                                                                               95 100                              64D.sup.a                                                                          -- 0  0   95 35 0  15 50  75  75 25 -- 75 40                               66D.sup.a                                                                          -- 0  15  15 50 20 50 100 100 75 0  -- 90 100                              67D.sup.a                                                                          -- 0  0   100                                                                               100                                                                               0  25 95  75  50 25 -- 30 75                               69D.sup.a                                                                          -- 30 0   100                                                                               100                                                                               0  70 100 100 100                                                                               35 -- 95 100                              70D.sup.a                                                                          -- 100                                                                               10  100                                                                               100                                                                               25 65 100 100 100                                                                               0  -- 95 100                              __________________________________________________________________________      (--) = Not tested.                                                             .sup.a Tested at 0.28 kg/ha.                                             

                                      TABLE V-D                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     34D 90 85 30  95 -- 45 98 75  100 100                                                                               40 100                                                                               50 --                               35D 100                                                                               85 70  100                                                                               -- 90 100                                                                               100 100 100                                                                               40 100                                                                               75 --                               40D 100                                                                               100                                                                               20  100                                                                               -- 70 100                                                                               98  98  100                                                                               20 100                                                                               50 --                               41D 100                                                                               100                                                                               80  100                                                                               -- 60 100                                                                               100 100 100                                                                               25 100                                                                               95 --                               42D 50 60 40  85 -- 30 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 --                               43D 90 95 60  100                                                                               -- 30 98 100 98  100                                                                               45 100                                                                               95 --                               44D 60 100                                                                               20  100                                                                               -- 60 100                                                                               100 90  100                                                                               20 100                                                                               80 --                               45D 95 100                                                                               35  100                                                                               -- 60 90 100 100 100                                                                               0  100                                                                               90 --                               46D 100                                                                               100                                                                               90  100                                                                               -- 95 100                                                                               100 100 100                                                                               40 100                                                                               95 --                               47D 100                                                                               100                                                                               100 100                                                                               -- 98 100                                                                               100 98  100                                                                               30 100                                                                               95 --                               48D 100                                                                               100                                                                               100 100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               100                                                                               --                               49D 100                                                                               100                                                                               100 100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               -- --                               50D 100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               90 100                                                                               98 --                               54D 100                                                                               100                                                                               85  100                                                                               100                                                                               15 100                                                                               25  100 100                                                                               65 100                                                                               95 100                              55D 85 100                                                                               35  100                                                                               98 15 100                                                                               15  100 100                                                                               65 100                                                                               95 --                               56D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               100                              58D 98 100                                                                               40  95 40 20 95 100 100 100                                                                               85 100                                                                               100                                                                               95                               59D 100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               100                                                                               100                                                                               85 80                               60D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               75 100                                                                               85 80                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VI-D                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     61D -- 100                                                                               65  100                                                                               65 20 80 20  40  80 10                                                                               -- 20 0                                 62D -- 50 35  70 50 0  0  0   25  50 0 -- 0  0                                 63D 100                                                                               100                                                                               100 100                                                                               100                                                                               95 100                                                                               90  95  100                                                                               75                                                                               100                                                                               100                                                                               85                                68D -- 0  20  0  0  0  0  60  100 100                                                                               90                                                                               -- 75 75                                71D -- 50 40  50 75 40 35 75  50  70 0 -- 75 75                                72D -- 35 60  100                                                                               85 50 100                                                                               25  65  100                                                                               35                                                                               -- 100                                                                               35                                73D -- 90 70  100                                                                               95 25 0  70  100 100                                                                               0 -- 50 25                                __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VII-D                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      7D 100                                                                               100                                                                               100 100                                                                               80 90 10 95  100 100                                                                               55 100                                                                               45 100                              16D.sup.a                                                                          100                                                                               85 35  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               85 70                               24D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               29D 100                                                                               100                                                                               60  100                                                                               90 100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               33D 90 98 85  100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               90 100                                                                               90 100                              53D 100                                                                               100                                                                               60  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               57D 25 40 10  100                                                                               10 0  10 100 95  100                                                                               35 100                                                                               -- 100                              64D.sup.a                                                                          -- 0  0   90 0  0  85 40  100 80 50 -- 35 100                              65D.sup.a                                                                          -- 0  0   65 0  0  70 75  80  75 0  -- 25 75                               67D.sup.a                                                                          -- 0  0   75 35 0  40 70  80  60 0  -- 0  100                              69D.sup.a                                                                          -- 0  0   80 35 0  100                                                                               90  100 100                                                                               40 -- 35 100                              70D.sup.a                                                                          -- 100                                                                               0   100                                                                               70 90 90 100 100 100                                                                               30 -- 25 100                              __________________________________________________________________________      (--) = Not tested.                                                             .sup.a Tested at 0.28 kg/ha.                                             

                                      TABLE VIII-D                                 __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     34D 90 85 30  95 -- 45 98 75  100 100                                                                               40 100                                                                               50 --                               35D 100                                                                               85 70  100                                                                               -- 90 100                                                                               100 100 100                                                                               40 100                                                                               75 --                               40D 75 100                                                                               5   100                                                                               -- 50 75 100 100 100                                                                               40 100                                                                               30 --                               41D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               42D 40 100                                                                               35  100                                                                               -- 50 80 100 100 100                                                                               80 100                                                                               70 --                               43D 60 70 20  100                                                                               -- 55 60 100 100 100                                                                               95 100                                                                               70 --                               44D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               45D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               46D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               47D 90 100                                                                               35  100                                                                               -- 75 90 100 100 100                                                                               25 100                                                                               45 --                               48D 80 100                                                                               60  100                                                                               -- 60 80 100 100 100                                                                               85 100                                                                               60 --                               49D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               50D 90 80 60  95 80 90 100                                                                               100 100 100                                                                               65 100                                                                               80 --                               54D 35 50 30  100                                                                               30 15 90 100 100 100                                                                               100                                                                               100                                                                               95 --                               55D 100                                                                               100                                                                               20  100                                                                               90 20 100                                                                               90  100 100                                                                               100                                                                               100                                                                               -- --                               56D 75 90 75  95 90 25 100                                                                               100 100 100                                                                               90 100                                                                               90 100                              58D 70 100                                                                               40  100                                                                               95 30 95 100 95  100                                                                               95 100                                                                               95 85                               59D 90 100                                                                               95  100                                                                               100                                                                               50 100                                                                               100 100 100                                                                               95 100                                                                               100                                                                               95                               60D 95 100                                                                               100 100                                                                               100                                                                               75 95 100 100 100                                                                               95 100                                                                               100                                                                               100                              __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IX-D                                   __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     61D -- 40 0   50 35 0  40 75  95  100                                                                               0  -- 25 50                               62D -- 35 0   20 0  0  20 35  60  100                                                                               0  -- 0  100                              63D 100                                                                               100                                                                               85  98 85 100                                                                               100                                                                               100 100 100                                                                               100                                                                               85 85 95                               68D -- 30 40  85 0  25 60 80  95  100                                                                               95 -- 0  80                               71D -- 50 0   80 65 0  75 100 80  100                                                                               50 -- 25 100                              72D -- 90 70  80 50 50 75 85  100 100                                                                               90 -- 100                                                                               100                              73D -- 100                                                                               15  100                                                                               75 75 85 100 100 90 60 -- 80 100                              __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IV-E                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                   __________________________________________________________________________     17E 95 85 35  100                                                                               85                                                                               25 90 100 100 100                                                                               40                                                                               100                                                                               95                                    18E 0  0  0   50 20                                                                               0  15 60  45  100                                                                               0 100                                                                               --                                    __________________________________________________________________________

                                      TABLE V-E                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicde Test                                         Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                 __________________________________________________________________________      7E 30 70 20  100                                                                               75 0  90 100 95  100                                                                               100                                                                               100                                                                               90                                   8E 95 95 45  100                                                                               98 25 90 100 95  100                                                                               90 100                                                                               90                                   9E 10 70 40  100                                                                               20 0  80 100 85  100                                                                               40 100                                                                               95                                  10E 100                                                                               100                                                                               10  100                                                                               40 0  90 100 100 100                                                                               80 100                                                                               100                                 11E 90 100                                                                               90  100                                                                               100                                                                               65 100                                                                               100 90  100                                                                               30 100                                                                               65                                  12E 100                                                                               100                                                                               80  100                                                                               100                                                                               85 90 100 100 100                                                                               85 100                                                                               90                                  13E 0  100                                                                               10  100                                                                               100                                                                               80 70 80  90  100                                                                               70 100                                                                               80                                  15E 0  10 0   90 0  0  15 35  30  100                                                                               10 85 75                                  19E 100                                                                               90 0   100                                                                               20 10 40 95  100 100                                                                               100                                                                               100                                                                               65                                  __________________________________________________________________________

                                      TABLE VI-E                                   __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                   __________________________________________________________________________     17E 80 100                                                                               55  95 90                                                                               20 60 100 100 100                                                                               75                                                                               100                                                                               70                                    18E 0  100                                                                               0   98 20                                                                               0  10 70  60  100                                                                               10                                                                               100                                                                               45                                    __________________________________________________________________________

                                      TABLE VII-E                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Applicaton Rate - 1.12 kg/ha                                                   Cmpd.                                                                          No. DB FT ARG WG JG                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                   __________________________________________________________________________      7E 25 30 0   70 60                                                                               20 90 75  95  85 50                                                                               100                                                                               35                                     8E 80 80 20  70 70                                                                               40 80 50  80  80 60                                                                               60 35                                     9E 0  30 0   75 15                                                                               25 100                                                                               95  100 100                                                                               60                                                                               100                                                                               25                                    10E 60 80 20  70 35                                                                               25 80 75  90  90 70                                                                               100                                                                               45                                    11E 45 100                                                                               20  100                                                                               100                                                                              40 50 100 100 100                                                                               20                                                                               100                                                                               35                                    12E 70 60 30  100                                                                               100                                                                              80 98 90  100 100                                                                               70                                                                               98 40                                    13E 25 100                                                                               10  100                                                                               100                                                                              85 100                                                                               80  100 100                                                                               10                                                                               90 25                                    15E 30 65 10  90 50                                                                               30 20 85  80  98 30                                                                               65 15                                    19E 20 60 10  90 10                                                                               15 90 100 100 70 100                                                                              40 85                                    __________________________________________________________________________

                                      TABLE IV-F                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     19F 40 35 60  100                                                                               90 30 90 100 100 -- 20 100                                                                               90 --                               26F 25 70 45  95 60 25 85 35  75  -- 20 100                                                                               95 90                               27F 45 65 40  100                                                                               60 25 80 100 85  100                                                                               40 100                                                                               95 35                               28F 80 100                                                                               90  100                                                                               100                                                                               90 100                                                                               70  90  100                                                                               30 100                                                                               95 35                               29F 90 45 75  100                                                                               85 40 90 95  90  100                                                                               40 100                                                                               95 --                               30F 90 45 75  100                                                                               90 75 100                                                                               100 80  100                                                                               60 100                                                                               95 --                               31F 60 65 75  100                                                                               100                                                                               55 95 100 100 100                                                                               100                                                                               100                                                                               95 --                               32F 90 100                                                                               90  100                                                                               100                                                                               65 85 100 90  100                                                                               95 100                                                                               85 --                               33F 100                                                                               100                                                                               95  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               25 100                                                                               90 --                               35F 90 100                                                                               100 100                                                                               -- 90 90 100 90  100                                                                               10 100                                                                               75 --                               36F 90 35 85  100                                                                               -- 15 80 95  90  100                                                                               50 100                                                                               95 --                               39F 100                                                                               100                                                                               100 100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               100                                                                               100                                                                               98 --                               40F 100                                                                               100                                                                               80  100                                                                               100                                                                               70 100                                                                               100 100 100                                                                               90 100                                                                               95 --                               41F 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               60 100                                                                               98 --                               42F 60 100                                                                               85  100                                                                               100                                                                               70 95 100 95  100                                                                               10 100                                                                               95 50                               43F 85 100                                                                               25  100                                                                               60 25 98 100 100 100                                                                               100                                                                               100                                                                               90 100                              44F 0  80 10  85 0  0  75 0   30  100                                                                               0  100                                                                               0  10                               45F 25 100                                                                               40  100                                                                               60 0  65 60  60  100                                                                               50 100                                                                               70 0                                50F -- 100                                                                               50  100                                                                               35 35 75     100 100                                                                               --                                        __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE V-F                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     46F 0  65 35  75 65 0  0  0   35  100                                                                               25                                                                               90 80 0                                 47F -- 60 35  100                                                                               100                                                                               0  90 100 100 100                                                                               70                                                                               -- 100                                                                               75                                48F -- 75 20  90 60 0  15 70  35  90 0 -- 20 40                                49F -- 60 10  100                                                                               60 0  50 100 95  100                                                                               40                                                                               -- 90 100                               51F -- 40 10  95 40 10 50 65  100 100                                                                               0 -- 95 65                                __________________________________________________________________________      (--)  Not tested.                                                        

                                      TABLE VI-F                                   __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     19F 100                                                                               90 65  100                                                                               100                                                                               98 100                                                                               100 100 100                                                                               60 100                                                                               70 100                              26F 60 75 60  95 45 50 90 50  90  100                                                                               40 90 60 --                               27F 80 70 65  95 100                                                                               90 100                                                                               100 100 100                                                                               85 100                                                                               75 --                               28F 80 100                                                                               75  90 85 80 100                                                                               80  80  100                                                                               30 100                                                                               85 85                               29F 85 70 55  90 98 90 100                                                                               100 100 100                                                                               35 100                                                                               60 100                              30F 90 80 40  90 85 80 80 70  100 100                                                                               20 100                                                                               40 --                               31F 100                                                                               80 20  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               85 --                               32F 70 90 60  100                                                                               100                                                                               98 100                                                                               100 100 100                                                                               100                                                                               100                                                                               60 --                               33F 95 100                                                                               80  100                                                                               90 100                                                                               100                                                                               100 100 100                                                                               70 100                                                                               40 --                               35F 70 90 40  100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               98 100                                                                               30 --                               36F 85 100                                                                               35  100                                                                               -- 20 100                                                                               100 100 100                                                                               100                                                                               100                                                                               15 --                               39F 100                                                                               100                                                                               85  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 100                              40F 100                                                                               100                                                                               30  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               75 --                               41F 100                                                                               100                                                                               35  90 70 100                                                                               90 100 100 100                                                                               50 100                                                                               70 --                               42F 45 100                                                                               50  100                                                                               70 55 80 100 100 100                                                                               70 100                                                                               75 100                              43F 25 80 15  98 35 0  20 100 100 100                                                                               100                                                                               100                                                                               60 95                               44F 0  15 0   65 0  0  0  70  100 100                                                                               40 100                                                                               0  100                              45F 0  75 35  70 35 0  60 50  85  100                                                                               50 100                                                                               75 70                               50F -- 40 0   75 45 40 60 100 100 95 30 -- 60 100                              __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VII-F                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                 __________________________________________________________________________     46F 25 35 20  50 35                                                                               35 0  20  75  100                                                                               35                                                                               95 -- 50                                 47F -- 75 25  90 40                                                                               25 80 100 100 100                                                                               80                                                                               -- 75 100                                48F -- 50 35  80 35                                                                               40 0  75  100 85 15                                                                               -- 50 75                                 49F -- 35 0   75 30                                                                               0  20 100 100 100                                                                               80                                                                               -- 25 85                                 51F -- 35 0   80 35                                                                               20 70 50  95  95 25                                                                               -- 65 50                                 __________________________________________________________________________      (--) = Not Tested.                                                       

The compounds of the present invention and their salts are useful as herbicides and can be applied in a variety of ways at various concentrations. In practice, the compounds or salts are formulated into herbicidal compositions, by admixture, in herbicidally effective amounts, with the adjuvants and carriers normally employed for facilitating the dispersion of active ingredients for agricultural applications, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the materials in a given application. Thus, these active herbicidal compounds or salts can be formulated as granules of relatively large particle size, as wettable powders, as emulsifiable concentrates, as powdery dusts, as flowables, as solutions or as any of several other known types of formulations, depending upon the desired mode of application. These formulations may contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. A herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from about 0.01 to approximately 10 pounds per acre, preferably from about 0.02 to about 4 pounds per acre.

Wettable powders are in the form of finely divided particles which disperse readily in water or other dispersants. The wettable powder is ultimately applied to the soil either as a dry dust or as a dispersion in water or other liquid. Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic diluents. Wettable powders normally are prepared to contain about 5% to about 95% of the active ingredient and usually also contain a small amount of wetting, dispersing, or emulsifying agent to facilitate wetting and dispersion.

Emulsifiable concentrates are homogeneous liquid compositions which are dispersible in water or other dispersant, and may consist entirely of the active compound or salt with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthal, isophorone and other non-volatile organic solvents. For herbicidal application, these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises about 0.5% to 95% of active ingredient by weight of the herbicidal composition.

Granular formulations wherein the toxicant is carried on relatively coarse particles, are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite and other organic or inorganic materials which absorb or which may be coated with the toxicant. Granular formulations normally are prepared to contain about 0.1% to about 25% of active ingredients which may include surface-active agents such heavy aromatic naphthas, kerosene or other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.

Typical wetting, dispersing or emulsifying agents and adjuvants used in agricultural formulations include, for example, the alkyl and alkylaryl sulfonates and sulfates and their salts; polyhydric alcohols; polyethoxylated alcohols, esters and fatty amines; and other types of surface-active agents, many of which are available in commerce. The surface-active agent, when used, normally comprises from 0.1% to 30% by weight of the herbicidal composition.

Dusts, which are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers for the toxicant, are useful formulations for soil-incorporating application.

Pastes, which are homogeneous suspensions of a finely divided solid toxicant in a liquid carrier such as water or oil, are employed for specific purposes. These formulations normally contain about 5% to about 95% of active ingredient by weight, and may also contain small amounts of a wetting, dispersing or emulsifying agent to facilitate dispersion. For application, the pastes are normally diluted and applied as a spray to the area to be affected.

Other useful formulations for herbicidal applications include simple solutions of the active ingredient in a dispersant in which it is completely soluble at the desired concentration, such as water, acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprays, typically aerosols, wherein the active ingredient is dispersed in finely-divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used.

The phytotoxic compositions of this invention can be applied to the plants in the conventional manner. Thus, the dust and liquid compositions can be applied to the plant by the use of power-dusters, boom and hand sprayers and spray dusters. The compositions can also be applied from airplanes as a dust or a spray or by rope wick applications because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging seedlings, as a typical example, the dust and liquid compositions can be applied to the soil according to conventional methods and can be distributed in the soil to a depth of at least 1/2 inch below the soil surface. It is not necessary that the phytotoxic compositions be mechanically admixed with the soil particles since these compositions can also be applied merely by spraying or sprinkling the surface of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations. In the following examples the herbicidal compound can be substituted with the herbicidal salt of the compound.

    __________________________________________________________________________     Formula with Ranges  Specific Formula                                          __________________________________________________________________________     EMULSIFIABLE CONCENTRATE FORMULATIONS                                          Herbicidal compound                                                                           5-55  herbicidal compound                                                                          24                                          surfactant(s)  5-25  proprietary blend of oil-soluble                                                             10                                          solvent(s)     20-90 sulfonates and                                                           100%  polyoxyethylene ethers                                                         polar solvent 27                                                               petroleum hydrocarbon                                                                        39                                                                             100%                                        WETTABLE POWDER FORMULATIONS                                                   herbicidal compound                                                                            3-90 herbicidal compound                                                                          80                                          wetting agent  0.5-2 sodium dialkyl naphthalene                                                                   0.5                                         dispersing agent                                                                              1-8   sulfonate                                                 diluent(s)     8.5-87                                                                               sodium lignosulfonate                                                                        7                                                          100%  attapulgite clay                                                                             12.5                                                                           100%                                        EXTRUDED GRANULAR FORMULATIONS                                                 herbicidal compound                                                                            1-20 herbicidal compound                                                                          10                                          binding agent   0-10 lignin sulfonate                                                                             5                                           diluent(s)     70-99 calcium carbonate                                                                            85                                                         100%                100%                                        FLOWABLE FORMULATIONS                                                          herbicidal compound                                                                           20-70 herbicidal compound                                                                          45                                          surfactant(s)   1-10 polyoxyethylene ether                                                                        5                                           suspending agent(s)                                                                           0.05-1                                                                               attagel       0.05                                        antifreeze agent                                                                               1-10 propylene glycol                                                                             10                                          antimicrobial agent                                                                            1-10 1,2-benzisothiazoline-3-one                                                                  0.03                                        antifoam agent 0.1-1 silicone defoamer                                                                            0.02                                        solvent         7.95-77.85                                                                          water         39.9                                                       100%                100%                                        __________________________________________________________________________

When salts are used as the active ingredient in the herbicidal compositions of this invention it is recommended to use salts that are agriculturally acceptable.

The phytotoxic compositions of this invention can also contain other additives, for example, fertilizers, other herbicides and other pesticides, used as adjuvant or in combination with any of the above-described adjuvants. Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. 

We claim:
 1. A compound of the formula ##STR96## wherein R⁵⁰ is C₁ -C₄ alkyl optionally substituted with halogen;R⁵¹ is hydrogen or C₁ -C₄ alkyl; R⁵² is hydrogen, C₁ -C₄ alkyl or ##STR97## wherein R^(a) is C₁ -C₄ alkyl; or R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms; R⁵³ is hydrogen or C₁ -C₄ alkyl; R⁵⁴ is hydrogen or C₁ -C₄ alkyl; R⁵⁵ is hydrogen or C₁ -C₄ alkyl; R⁵⁶ is hydrogen or C₁ -C₄ alkyl; and R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁵⁷ is not attached to the 6-position and their salts.
 2. The compound of claim 1 wherein R⁵⁰ is methyl or trifluoromethyl; R⁵¹ is hydrogen or methyl; R⁵² is hydrogen or methyl; R⁵³ is hydrogen or methyl; R⁵⁴ is hydrogen or methyl; R⁵⁵ is hydrogen or methyl; R⁵⁶ is hydrogen or methyl; R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 3. The compound of claim 2 wherein R⁵⁷ and R⁵⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)-- where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R⁵⁷ is in the 3-position.
 4. The compound of claim 2 wherein R⁵⁷ is hydrogen and R⁵⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 5. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --
 6. The compound of claim 1 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is methyl; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 7. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is C₂ H₅ SO₂ --.
 8. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 9. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is methylthio.
 10. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is cyano.
 11. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is C₂ H₅ SO₂ --.
 12. The compound of claim 2 wherein R⁵⁰ is trifluoromethyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is methyl; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is bromine.
 13. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is 3-cyano; and R⁵⁸ is hydrogen.
 14. The compound of claim 2 wherein R⁵⁰ is trifluoromethyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is ethylthio.
 15. The compound of claim 2 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is 3-nitro; and R⁵⁸ is hydrogen.
 16. The compound of claim 2 wherein R⁵⁷ is hydrogen.
 17. The compound of claim 3 wherein R⁵⁷ is hydrogen.
 18. The compound of claim 1 wherein R⁵¹ and R⁵² are hydrogen or both methyl.
 19. The compound of claim 18 wherein R⁵⁸ is --SO₂ CH₃.
 20. The compound of claim 18 wherein R⁵⁸ is --SO₂ CH₂ Cl.
 21. The compound of claim 1 wherein R⁵⁸ is trifluoromethyl.
 22. The compound of claim 1 wherein R⁵⁸ is --SO₂ CH₃.
 23. The compound of claim 1 wherein R⁵⁸ is cyano.
 24. The compound of claim 1 wherein R⁵⁸ is --SO₂ CH₂ Cl.
 25. The compound of claim 1 wherein R⁵⁸ is --SO₂ C₂ H₅.
 26. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula ##STR98## wherein R⁵⁰ is C₁ -C₄ alkyl optionally substituted with halogen;R⁵¹ is hydrogen or C₁ -C₄ alkyl; R⁵² is hydrogen, C₁ -C₄ alkyl or ##STR99## wherein R^(a) is C₁ -C₄ alkyl; or R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms; R⁵³ is hydrogen or C₁ -C₄ alkyl; R⁵⁴ is hydrogen or C₁ -C₄ alkyl; R⁵⁵ is hydrogen or C₁ -C₄ alkyl; R⁵⁶ is hydrogen or C₁ -C₄ alkyl; and R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁵⁷ is not attached to the 6-position or its salts.
 27. The method of claim 26 wherein R⁵⁰ is methyl or trifluoromethyl; R⁵¹ is hydrogen or methyl; R⁵² is hydrogen or methyl; R⁵³ is hydrogen or methyl; R⁵⁴ is hydrogen or methyl; R⁵⁵ is hydrogen or methyl; R⁵⁶ is hydrogen or methyl; R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 28. The method of claim 27 wherein R⁵⁷ and R⁵⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)-- where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R⁵⁷ is in the 3-position.
 29. The method of claim 27 wherein R⁵⁷ is hydrogen and R⁵⁸ is hydrogen; chlorine; bromine; fluorine; trifluoromethyl; or R² SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 30. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 31. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is methyl; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 32. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is C₂ H₅ SO₂ --.
 33. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 34. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is methylthio.
 35. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is cyano.
 36. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is C₂ H₅ SO₂ --.
 37. The method of claim 27 wherein R⁵⁰ is trifluoromethyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is methyl; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is bromine.
 38. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is 3-cyano; and R⁵⁸ is hydrogen.
 39. The method of claim 27 wherein R⁵⁰ is trifluoromethyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is ethylthio.
 40. The method of claim 27 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is 3-nitro; and R⁵⁸ is hydrogen.
 41. The method of claim 27 wherein R⁵⁷ is hydrogen.
 42. The method of claim 28 wherein R⁵⁷ is hydrogen.
 43. The method of claim 26 wherein R⁵¹ and R⁵² are hydrogen or both methyl.
 44. The method of claim 43 wherein R⁵⁸ is --SO₂ CH₃.
 45. The method of claim 43 wherein R⁵⁸ is --SO₂ CH₂ Cl.
 46. The method of claim 26 wherein R⁵⁸ is trifluoromethyl.
 47. The method of claim 26 wherein R⁵⁸ is --SO₂ CH₃.
 48. The method of claim 26 wherein R⁵⁸ is cyano.
 49. The method of claim 26 wherein R⁵⁸ is --SO₂ CH₂ Cl.
 50. The method of claim 26 wherein R⁵⁸ is --SO₂ C₂ H₅.
 51. A herbicidal composition comprising a herbicidally active 2-(2-substituted benzoyl)-1,3-cyclohexanedione or its salts and an inert carrier therefor wherein the 2-benzoyl substituent is C₁ -C₄ alkyl optionally substituted with halogen.
 52. The herbicidal composition of claim 51 wherein the 2-(2-substituted benzoyl)-1,3-cyclohexanedione is a compound of the formula ##STR100## wherein R⁵⁰ is C₁ -C₄ alkyl optionally substituted with halogen;R⁵¹ is hydrogen or C₁ -C₄ alkyl; R⁵² is hydrogen, C₁ -C₄ alkyl or ##STR101## wherein R^(a) is C₁ -C₄ alkyl; or R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms; R⁵³ is hydrogen or C₁ -C₄ alkyl; R⁵⁴ is hydrogen or C₁ -C₄ alkyl; R⁵⁵ is hydrogen or C₁ -C₄ alkyl; R⁵⁶ is hydrogen or C₁ -C₄ alkyl; and R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ halo alkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁵⁷ is not attached to the 6-position.
 53. The composition of claim 52 wherein R⁵⁰ is methyl or trifluoromethyl; R⁵¹ is hydrogen or methyl; R⁵² is hydrogen or methyl; R⁵³ is hydrogen or methyl; R⁵⁴ is hydrogen or methyl; R⁵⁵ is hydrogen or methyl; R⁵⁶ is hydrogen or methyl; R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 54. The composition of claim 53 wherein R⁵⁷ is hydrogen.
 55. The composition of claim 53 wherein R⁵⁷ and R⁵⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)-- where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R⁵⁷ is in the 3-position.
 56. The composition of claim 55 wherein R⁵⁷ is hydrogen.
 57. The composition of claim 53 wherein R⁵⁷ is hydrogen and R⁵⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethoxy or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 58. The composition of claim 53 wherein R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 59. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is methyl; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 60. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is C₂ H₅ SO₂ --.
 61. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is CH₃ SO₂ --.
 62. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is methylthio.
 63. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is cyano.
 64. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is C₂ H₅ SO₂ --.
 65. The herbicidal composition of claim 53 wherein R⁵⁰ is trifluoromethyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is methyl; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is bromine.
 66. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is hydrogen; R⁵² is hydrogen; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is 3-cyano; and R⁵⁸ is hydrogen.
 67. The herbicidal composition of claim 53 wherein R⁵⁰ is trifluoromethyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is hydrogen; and R⁵⁸ is ethylthio.
 68. The herbicidal composition of claim 53 wherein R⁵⁰ is methyl; R⁵¹ is methyl; R⁵² is methyl; R⁵³ is hydrogen; R⁵⁴ is hydrogen; R⁵⁵ is hydrogen; R⁵⁶ is hydrogen; R⁵⁷ is 3-nitro; and R⁵⁸ is hydrogen.
 69. The herbicidal composition of claim 53 wherein R⁵¹ is methyl, R⁵² is methyl, R⁵³ is hydrogen, R⁵⁴ is hydrogen, R⁵⁵ is hydrogen, R⁵⁶ is hydrogen, R⁵⁷ is hydrogen and R⁵⁸ is ClCH₂ SO₂.
 70. The herbicidal composition of claim 51 wherein the 2-(2-benzoyl)-1,3-cyclohexanedione has a C₁ -C₄ alkylsulfonyl or C₁ -C₄ haloalkylsulfonyl substitition on the phenyl ring.
 71. The herbicidal composition of claim 70 wherein said alkylsulfonyl or haloalkylsulfonyl substitution is at the 4-position of the phenyl ring.
 72. The herbicidal composition of claim 51 where the 2-(2-benzoyl)-1,3-cyclohexanedione has a C₁ -C₄ haloalkyl substitution on the phenyl ring.
 73. The herbicidal composition of claim 72 wherein said haloalkyl substitution is at the 4-position of the phenyl ring.
 74. The herbicidal composition of claim 72 wherein said haloalkyl is trifluoromethyl.
 75. The composition of matter of claim 52 wherein R⁵¹ and R⁵² are hydrogen or both methyl.
 76. The composition of matter of claim 75 wherein R⁵⁸ is --SO₂ CH₃.
 77. The composition of matter of claim 75 wherein R⁵⁸ is --SO₂ CH₂ Cl.
 78. The composition of matter of claim 52 wherein R⁵⁸ is trifluoromethyl.
 79. The composition of matter of claim 52 wherein R⁵⁸ is --SO₂ CH₃.
 80. The composition of matter of claim 52 wherein R⁵⁸ is cyano.
 81. The composition of matter of claim 52 wherein R⁵⁸ is --SO₂ CH₂ Cl.
 82. The composition of matter of claim 52 wherein R⁵⁸ is --SO₂ C₂ H₅.
 83. The method of controlling undesirable vegetation comprising applying to the area where control is desired, a herbicidal composition comprising a herbicidally active 2-(2-benzoyl)-1,3-cyclohexanedione and an inert carrier therefor wherein the 2-position of the benzoyl moiety is substituted with C₁ -C₄ alkyl, optionally substituted with halogen.
 84. The method of claim 83 wherein the 2-(2-benzoyl)-1,3-cyclohexanedione has a C₁ -C₄ alkylsulfonyl or C₁ -C₄ haloalkylsulfonyl substitution on the phenyl ring.
 85. The method of claim 84 wherein said alkylsulfonyl or haloalkylsulfonyl substitution is at the 4-position of the phenyl ring.
 86. The method of claim 83 wherein the 2-(2-benzoyl)-1,3-cyclohexanedione has a C₁ -C₄ haloalkyl substitution on the phenyl ring.
 87. The method of claim 86 wherein said haloalkyl substitution is at the 4-position on the phenyl ring.
 88. The method of claim 86 wherein said haloalkyl is trifluoromethyl. 